Name: 36209-51-5|4-Amino-5-(pyridin-4-yl)-4H-1,2,4-triazole-3-thiol|95%
Brand: Ambeed
SKU: A650781
Price: 21.0 USD
Availability: InStock
Rating: 91 (25 reviews)

1
[ 36209-51-5 ]
[ 51395-52-9 ]
[ 133842-65-6 ]

Reference： [1]Journal of the Indian Chemical Society,1990,vol. 67,p. 864 - 865

2
[ 61019-32-7 ]
[ 36209-51-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	With hydrazine hydrate at 140 - 160℃; for 6h;
80%	With hydrazine hydrate In water for 3h; Reflux;
78%	With hydrazine hydrate In water Heating;

78%	With hydrazine hydrate In water for 4h; Reflux;	2.1.2. Synthesis of 4-amino-5-(pyridin-4-yl)-4H-1,2,4-triazole-3-thiol [16] (3) Potassium dithiocarbazinate salt (2) (0.079 mol) reacted with aqueous hydrazine hydrate (12 mL, 0.24 mol) solution and refluxed for 4h, hydrogen sulfide (H2S gas) evolved during the reaction was observed and indicated by the lead acetate solution (confirmatory test-turn lead acetate soaked filter paper converted from white to black). The reaction mixture was cooled to room temperature, diluted with ice-cold distilled water and subsequent acidification was performed with dilute acetic acid. Obtained light yellow precipitate was filtered, washed with cold distilled water and dried. Recrystallization was done using absolute ethanol to get white crystals (3). The compound 3 exists in thione-thiol tautomeric forms, but our investigation showed that in this case, the thiol structure dominated in the solid state, as indicated by the IR and NMR data of the compound. Yield: 78%, m.p. : 214-216°C; IR (cm-1): 3160 (N-H), 3000 (C-H), 2582 (S-H), 1608 (C=N), 1571 (C=C), 709 (out of plane C-H bending), 689 (C-S). 1H NMR (ppm): 3.77 (s,1H, -NH2), 10.51 (Aromatic C-SH), 7.92 (d, 1H,), 8.59 (d, 1H,); 13C NMR (ppm): 151.1 (), 134.0 (C1), 121.3 (C2 & C6). 149.8 (C3 & C5), LC-MS m/z: 193.23.
73%	With hydrazine hydrate for 0.133333h; microwave irradiation;
70%	With hydrazine hydrate In water for 24h; Reflux;	19.3 Step 3: Add 25.14 g (0.1 mol) of potassium salt and 20.0 g (0.4 mol) of hydrazine hydrate (NH 2 NH 2 ·H 2 O) to 100 mL of water.Reflow reaction for 24h,After the reaction, the hydrochloric acid was adjusted to pH 1,filter,Recrystallization,13.5 g (0.07 mmol) of the product 4-amino-3-(4-pyridyl)-1H-1,2,4-triazole-5H-thiol are obtained.The yield was 70%.
68%	With hydrazine hydrate Reflux;
67%	With hydrazine hydrate In water at 20℃; Reflux;
62%	With hydrazine hydrate In water for 1h; Reflux;
60%	Stage #1: potassium 4-pyridinyldithiocarbazate With hydrazine hydrate for 0.0333333h; Microwave irradiation; Stage #2: With hydrogenchloride In water for 0.0333333h;	Method B - Microwave Potassium salt of pyridine-4-dithiocarbazinic acid picolinic (1 g, 4 mmol) and hydrazine hydrate 99% (0.4 mL, 8 mmol) was taken in a 100 mL RB flask.The RB flask was then connected with a specially designed apparatus containing lead acetate powder (Ref 8). The lead acetate works as a trap for hydrogensulphide, emitted during the reaction. Microwave irradiation was carried out for 2 min at 900 MHz till a white solid appeared at the bottom or the H2S emission ceased. The solid was taken in 15-20 mL of water and acidified with concentrated hydrochloric acid. The white precipitate obtained was washed to neutral pH with water, dried and purified by recrystallization using methanol. The triazole was obtained as white crystalline solid. The homogeneity was checked by melting point and TLC using ethyl acetate methanol (1:1) as developping solvent and iodine vapor as visualizing agent (m.p. 218°C. Rf 0.42; Yield 5.7 g, 60.0%).
56%	With hydrazine hydrate
52%	With hydrazine In water for 2h; Heating;
	With hydrazine hydrate at 120℃;
	With hydrazine hydrate In water for 20h; Reflux;
	With hydrazine hydrate In water for 8h; Reflux;
	With hydrazine hydrate In water Reflux;	4.2. Preparation of 4-amino-5-(pyridin-4-yl)-4H-1,2,4-triazole-3-thiol (3) The above potassium dithiocarbazinate 2 was taken in water (8 mL) and hydrazine hydrate (2 mmol) and refluxed for 4-5 h. During progress of the reaction, the reaction mixture turned to green with evolution of hydrogen sulfide and finally it became homogeneous. It was then diluted with little cold water and acidified with conc. hydrochloric acid. The white precipitated solid was filtered, washed with cold water and recrystallized from aqueous methanol. 4-Amino-5-(pyridin-4-yl)-4H-1,2,4-triazole-3-thiol 3 displayed spectroscopic data consistent with those observed previously [27].
	With hydrazine hydrate In ethanol	General procedure for the synthesis of ligands L¹-L² General procedure: Intermediate triazoles 3a was synthesized from corresponding acid hydrazide (1a) through multi-step reactions (Scheme 1) as per the reported literature [13-14]. The hydrazide was converted to potassium salt (2a) by reacting with carbon disulfide and potassium hydroxide in absolute ethanol. On reacting with hydrazine hydrate, the salt undergoes ring closure to yield the triazole, 3a. The desired Schiff base L1 was obtained in good yield by refluxing equimolar amount of 4-amino-5-(pyridin-4-yl)-4H-1,2,4-triazole-3-thiol (3a) with thiophene-2-carbaldehyde using acetic acid as a solvent. The mixture was stirred at room temperature for 10 h (Scheme 1). The reaction mixture was kept overnight, pale yellow product was precipitated out. It was filtered, washed with ice cold water, methanol and recrystallized with a mixture of DMF & methanol. The same procedure was used for the synthesis of ligand L2.
	With hydrazine hydrate In water
	With hydrazine hydrate In water Reflux;
	With hydrazine hydrate for 5h; Reflux;
	Stage #1: potassium 4-pyridinyldithiocarbazate With hydrazine hydrate at 20℃; Stage #2: With water at 20℃; for 7h; Reflux;
	With hydrazine hydrate for 5h; Reflux;	1.4 (4) Synthesis of 4-amino-5-(pyridin-4-yl)-4H-1,2,4-triazole-3-mercapto (V) The above-prepared (IV) (10 mmol) and hydrazine hydrate (15 mmol), heating reflux reaction 5h, after completion of the reaction, 50 ml of water was added to the reaction solution, acidified with dilute hydrochloric acid, precipitated and filtered. The filter cake was washed with water (10 ml* ) and dried to give a white solid (V).
7.7502 g	With hydrazine hydrate at 143℃; for 4h;	1.1.2 The second step: the synthetic route of compound C is as follows:Will be 12.9844g (0.0517mol)The first step is to obtain compound D with 20 mL (0.41 mol)The mass percentage is 80% hydrazine hydrate,After magnetic stirring under reflux in an oil bath at 143 ° C for 4 h,The obtained product was mixed with 20 mL of ice water, and then adjusted to pH = 5 with concentrated hydrochloric acid to give a white solid, which was then filtered and dried in vacuo to give Compound C as a white solid. Yield:7.7502 g, yield: 77.6%.
	With hydrazine hydrate for 10h; Reflux;
	With hydrazine hydrate at 143℃; for 4h;
	Multi-step reaction with 2 steps 1: hydrazine hydrate / water / 12 h / 100 °C 2: hydrazine hydrate; pyridine / 12 h / 120 °C
	Stage #1: potassium 4-pyridinyldithiocarbazate With hydrazine hydrate Reflux; Stage #2: With hydrogenchloride In water

Reference： [1]Chande; Karnik; Inamdar; Ganguly [Journal of the Indian Chemical Society, 1990, vol. 67, # 3, p. 220 - 222]
[2]Location in patent: experimental part Mobinikhaledi, Akbar; Foroughifar, Naser; Bayat, Mahsa [Organic Preparations and Procedures International, 2011, vol. 43, # 4, p. 368 - 371]
[3]Sachdeva, Harshita; Dwivedi, Diksha; Arya, Kapil; Khaturia, Sarita; Saroj, Rekha [Medicinal Chemistry Research, 2013, vol. 22, # 10, p. 4953 - 4963]
[4]Rajoriya, Vaibhav; Kashaw, Varsha; Kashaw, Sushil K. [Letters in drug design and discovery, 2018, vol. 15, # 5, p. 451 - 462]
[5]Joshi; Karnik [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 4, p. 1057 - 1059]
[6]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES; Shanghai Institute of Materia Medica (in: CAS) - CN104892639, 2018, B Location in patent: Paragraph 0052; 0053; 0057
[7]Location in patent: scheme or table Gilani, Sadaf J.; Khan, Suroor A.; Siddiqui, Nadeem [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 16, p. 4762 - 4765]
[8]Li, Ziqiang; Liu, Yishuang; Bai, Xiaoguang; Deng, Qi; Wang, Juxian; Zhang, Guoning; Xiao, Chunling; Mei, Yaning; Wang, Yucheng [RSC Advances, 2015, vol. 5, # 118, p. 97089 - 97101]
[9]Location in patent: experimental part Chhabria, Mahesh T.; Suhagia, Bhanubhai N.; Brahmkshatriya, Pathik S.; Raval, Priyesha M. [Arzneimittel-Forschung/Drug Research, 2011, vol. 61, # 8, p. 452 - 457]
[10]Majumder, Sujan; Bashyal, Bishnu Maya; Gupta [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 10, p. 1260 - 1274]
[11]Sasaki, Tadashi; Ito, Eikoh [Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 1353 - 1356]
[12]Pandeya, Surendra N.; Sriram, Dharmarajan; Nath, Gopal; De Clercq, Erik [Arzneimittel-Forschung/Drug Research, 2000, vol. 50, # 1, p. 55 - 59]
[13]Li, Dejiang; Long, Deqing; Fu, Heqing [Phosphorus, Sulfur and Silicon and the Related Elements, 2006, vol. 181, # 3, p. 519 - 526]
[14]Location in patent: experimental part Foroughifar, Naser; Mobinikhaledi, Akbar; Ebrahimi, Sattar; Fard, Mohammad Ali Bodaghi; Moghanian, Hassan [Journal of the Chinese Chemical Society, 2009, vol. 56, # 5, p. 1043 - 1047]
[15]Location in patent: experimental part Singh, Ram Janam; Singh, Dharmendra Kumar [Journal of the Chemical Society of Pakistan, 2010, vol. 32, # 2, p. 235 - 239]
[16]Khan, Imtiaz; Zaib, Sumera; Ibrar, Aliya; Rama, Nasim Hasan; Simpson, Jim; Iqbal, Jamshed [European Journal of Medicinal Chemistry, 2014, vol. 78, p. 167 - 177]
[17]Tyagi, Prateek; Chandra, Sulekh; Saraswat; Yadav, Deepak [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2015, vol. 145, p. 155 - 164]
[18]Xu, Yong-Peng; Chen, Yue-Hu; Chen, Zhi-Jian; Qin, Jie; Qian, Shao-Song; Zhu, Hai-Liang [European Journal of Inorganic Chemistry, 2015, vol. 2015, # 12, p. 2076 - 2084]
[19]Khan, Imtiaz; Panini, Piyush; Khan, Salah Ud-Din; Rana, Usman Ali; Andleeb, Hina; Chopra, Deepak; Hameed, Shahid; Simpson, Jim [Crystal Growth and Design, 2016, vol. 16, # 3, p. 1371 - 1386]
[20]Ding, Xiao-Min; Zhai, Zhi-Wen; Lv, Lu-Ping; Sun, Zhao-Hui; Liu, Xing-Hai [Journal of the Chemical Society of Pakistan, 2016, vol. 38, # 5, p. 990 - 995]
[21]Li, Ziqiang; Bai, Xiaoguang; Deng, Qi; Zhang, Guoning; Zhou, Lei; Liu, Yishuang; Wang, Juxian; Wang, Yucheng [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 1, p. 213 - 220]
[22]Current Patent Assignee: ZHEJIANG UNIVERSITY OF TECHNOLOGY - CN106699776, 2017, A Location in patent: Paragraph 0024-0025; 0027; 0034-0035
[23]Current Patent Assignee: HUAIHUA UNIVERSITY - CN109438417, 2019, A Location in patent: Paragraph 0079; 0084-0086
[24]Slaihim, Mukhlif Mohsin; Al-Suede, Fouad Saleih R.; Khairuddean, Melati; Khadeer Ahamed, Mohamed B.; Shah Abdul Majid, Amin Malik [Journal of Molecular Structure, 2019, vol. 1196, p. 78 - 87]
[25]Jiang, Xia; Tang, Genyun; Yang, Jie; Ding, Jiacheng; Lin, Hongwei; Xiang, Xiaoliang [RSC Advances, 2020, vol. 10, # 32, p. 18927 - 18935]
[26]Current Patent Assignee: Syngenta (in: Sinochem Holdings); SINOCHEM HOLDINGS CORPORATION LTD - WO2021/64073, 2021, A1
[27]Fang, Zi-Mian; Guo, Deng-Xuan; Ji, Jin; Liu, Li-Wei; Qi, Pu-Ying; Shao, Wu-Bin; Wang, Jin-Jing; Wang, Pei-Yi; Yang, Song; Zhou, Xiang [Journal of Agricultural and Food Chemistry, 2021, vol. 69, # 50, p. 15108 - 15122]

3
potassium 2-isonicotinoyl hydrazine carbothionate [ No CAS ]
[ 36209-51-5 ]

Yield	Reaction Conditions	Operation in experiment
62%	With hydrazine hydrate In water for 8h; Reflux;	Synthesis of 4-amino-5-pyridinyl-4H-1,2,4-triazole3-thiol (2) Potassium hydroxide (8.4g, 150 mmol) wasdissolved in absolute ethanol (200 mmol). To the above solution isoniazide (13.7g, 100 mmol) was added and cooled the solution in ice. To this carbon disulphide was added in small portions with constant stirring.The reaction was agitated continuously for a period of 16 hr. It was then diluted with anhydrous ether (100ml) and dried under vacuum. The potassium-2-isonicotinoyl hydrazine carbothionate thus obtained was in quantitative yield and was used in next step without further purification. A suspension of salt (8.0g,100 mmol), hydrazine hydrate 99% (15 ml, 300 mmol) and water (5 ml) was refluxed for 8 hr. When evolution of hydrogen sulphide ceased and a clear solution resulted. It was then diluted with cold water (50 ml) and acidified with dilute hydrochloric acid to obtain a creamy white precipitate. The product was filtered,washed with cold water and recrystallized from aqueous ethanol. M.P. 2600, yield 62%.
	With hydrazine hydrate In water for 1h; Heating; Yield given;

Reference： [1]Ramjith; Muhammed Shakkeel; Nabeel [Indian Journal of Heterocyclic Chemistry, 2013, vol. 23, # 2, p. 155 - 158]
[2]Sung; Lee [Journal of Heterocyclic Chemistry, 1992, vol. 29, # 5, p. 1101 - 1109]

4
[ 36209-51-5 ]
[ 70-11-1 ]
[ 56400-87-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	In ethanol at 95℃; for 0.5h; Microwave irradiation;	1 5.3. Synthetic procedure and analytical data of 3,6-disubstituted triazolothiadiazines (6a-g) General procedure: A mixture of 5a (0.05 g, 0.26 mmol) and 2-bromoacetophenone (0.057 g, 0.29 mmol) were dissolved in absolute alcohol (2.5 mL), and the resulting mixture was heated at 95 °C in the microwave for 30 min. The mixture was allowed to stand overnight, separated solid was filtered, washed thoroughly with cold alcohol and ether, and dried to obtain 6a-1 (0.071 g, 93% yield) as a white solid: mp 226-227 °C
87%	In ethanol for 6h; Reflux;	4.1.4. General method for the preparation of compounds 5a,b General procedure: A mixture of 4-amino-5-pyridin-4-yl-4H-[1,2,4]triazole-3-thiol(2) (0.01 mol) and the appropriate phenacyl bromide (0.012 mol) in absolute ethanol was heated under reflux for 6 h. The reaction mixture was poured onto crushed ice and neutralized with Na2CO3.The solid product obtained was filtered, washed with water, dried and crystallized from ethanol.
81%	In ethanol for 24h; Heating;

65%

Stage #1: 4-amino-5-(pyridin-4-yl)-4H-1,2,4-triazole-3-thiol; α-bromoacetophenone In ethanol for 2h; Reflux; Stage #2: With ammonium hydroxide In ethanol at 20℃;

Reference： [1]Li, Ziqiang; Bai, Xiaoguang; Deng, Qi; Zhang, Guoning; Zhou, Lei; Liu, Yishuang; Wang, Juxian; Wang, Yucheng [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 1, p. 213 - 220]
[2]Kamel, Mona M.; Megally Abdo, Nadia Y. [European Journal of Medicinal Chemistry, 2014, vol. 86, p. 75 - 80]
[3]El Dawy; Omar; Ismail; Hazzaa [Journal of Pharmaceutical Sciences, 1983, vol. 72, # 1, p. 45 - 50]
[4]Location in patent: experimental part Hussein, Mostafa A.; Shaker, Refaat M.; Ameen, Mohammed A.; Mohammed, Mohammed F. [Archives of Pharmacal Research, 2011, vol. 34, # 8, p. 1239 - 1250]

5
[ 36209-51-5 ]
[ 619-41-0 ]
3-(pyridin-4-yl)-6-p-tolyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	In ethanol for 24h; Heating;
74%	In ethanol Reflux;	4.4. Preparation of 1,2,4-triazolo[3,4-b][1,3,4]-thiadiazines (6aeh) General procedure: A mixture of 4-amino-5-(pyridin-4-yl)-4H-[1,2,4]triazole-3-thiol 5 (1 mmol) and substituted phenacyl bromides (1.2 mmol) was refluxed in absolute ethanol (10 mL) for 6-7 h. The reactionmass was poured into crushed ice and neutralized with sodium bicarbonate. Solid product obtained was filtered, washed with water, dried and recrystallized from ethanol to afford conjugated products 6a-h [28].

Reference： [1]El Dawy; Omar; Ismail; Hazzaa [Journal of Pharmaceutical Sciences, 1983, vol. 72, # 1, p. 45 - 50]
[2]Khan, Imtiaz; Zaib, Sumera; Ibrar, Aliya; Rama, Nasim Hasan; Simpson, Jim; Iqbal, Jamshed [European Journal of Medicinal Chemistry, 2014, vol. 78, p. 167 - 177]

6
[ 36209-51-5 ]
[ 99-73-0 ]
6-(4-bromophenyl)-3-(pyridin-4-yl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	In ethanol for 6h; Reflux;	4.1.4. General method for the preparation of compounds 5a,b General procedure: A mixture of 4-amino-5-pyridin-4-yl-4H-[1,2,4]triazole-3-thiol(2) (0.01 mol) and the appropriate phenacyl bromide (0.012 mol) in absolute ethanol was heated under reflux for 6 h. The reaction mixture was poured onto crushed ice and neutralized with Na2CO3.The solid product obtained was filtered, washed with water, dried and crystallized from ethanol.
79%	In ethanol for 24h; Heating;
70%	Stage #1: 4-amino-5-(pyridin-4-yl)-4H-1,2,4-triazole-3-thiol; para-bromophenacyl bromide In ethanol for 2h; Reflux; Stage #2: With ammonium hydroxide In ethanol at 20℃;

Reference： [1]Kamel, Mona M.; Megally Abdo, Nadia Y. [European Journal of Medicinal Chemistry, 2014, vol. 86, p. 75 - 80]
[2]El Dawy; Omar; Ismail; Hazzaa [Journal of Pharmaceutical Sciences, 1983, vol. 72, # 1, p. 45 - 50]
[3]Location in patent: experimental part Hussein, Mostafa A.; Shaker, Refaat M.; Ameen, Mohammed A.; Mohammed, Mohammed F. [Archives of Pharmacal Research, 2011, vol. 34, # 8, p. 1239 - 1250]

7
[ 36209-51-5 ]
[ 2632-13-5 ]
6-(4-methoxyphenyl)-3-(pyridin-4-yl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	In ethanol at 95℃; for 0.5h; Microwave irradiation;	1 5.3. Synthetic procedure and analytical data of 3,6-disubstituted triazolothiadiazines (6a-g) General procedure: A mixture of 5a (0.05 g, 0.26 mmol) and 2-bromoacetophenone (0.057 g, 0.29 mmol) were dissolved in absolute alcohol (2.5 mL), and the resulting mixture was heated at 95 °C in the microwave for 30 min. The mixture was allowed to stand overnight, separated solid was filtered, washed thoroughly with cold alcohol and ether, and dried to obtain 6a-1 (0.071 g, 93% yield) as a white solid: mp 226-227 °C
78%	Stage #1: 4-amino-5-(pyridin-4-yl)-4H-1,2,4-triazole-3-thiol; 2-Bromo-4'-methoxyacetophenone In ethanol for 2h; Reflux; Stage #2: With ammonium hydroxide In ethanol at 20℃;
62%	In ethanol for 24h; Heating;

Reference： [1]Li, Ziqiang; Bai, Xiaoguang; Deng, Qi; Zhang, Guoning; Zhou, Lei; Liu, Yishuang; Wang, Juxian; Wang, Yucheng [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 1, p. 213 - 220]
[2]Location in patent: experimental part Hussein, Mostafa A.; Shaker, Refaat M.; Ameen, Mohammed A.; Mohammed, Mohammed F. [Archives of Pharmacal Research, 2011, vol. 34, # 8, p. 1239 - 1250]
[3]El Dawy; Omar; Ismail; Hazzaa [Journal of Pharmaceutical Sciences, 1983, vol. 72, # 1, p. 45 - 50]

8
[ 36209-51-5 ]
[ 20725-34-2 ]
6-(1-p-bromophenyl-5-methyl-1,2,3-triazol-4-yl)-3-(4-pyridyl)-s-triazolo[3,4-b]-1,3,4-thiadiazole [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1999,vol. 38,p. 380 - 383

9
[ 36209-51-5 ]
[ 210159-14-1 ]
6-(1-m-methylphenyl-5-methyl-1,2,3-triazol-4-yl)-3-(4-pyridyl)-s-triazolo[3,4-b]-1,3,4-thiadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With trichlorophosphate for 6h; Heating;

Reference： [1]Sun, Xiao-Wen; Zhang, Yan; Zhang, Zi-Yi; Wang, Qin; Wang, Shu-Fang [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 3, p. 380 - 383]

10
[ 36209-51-5 ]
[ 210159-08-3 ]
6-(1-m-bromophenyl-5-methyl-1,2,3-triazol-4-yl)-3-(4-pyridyl)-s-triazolo[3,4-b]-1,3,4-thiadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With trichlorophosphate for 6h; Heating;

Reference： [1]Sun, Xiao-Wen; Zhang, Yan; Zhang, Zi-Yi; Wang, Qin; Wang, Shu-Fang [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 3, p. 380 - 383]

11
[ 36209-51-5 ]
[ 88958-14-9 ]
6-(1-m-chlorophenyl-5-methyl-1,2,3-triazol-4-yl)-3-(4-pyridyl)-s-triazolo[3,4-b]-1,3,4-thiadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With trichlorophosphate for 6h; Heating;

Reference： [1]Sun, Xiao-Wen; Zhang, Yan; Zhang, Zi-Yi; Wang, Qin; Wang, Shu-Fang [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 3, p. 380 - 383]

12
[ 36209-51-5 ]
[ 210159-13-0 ]
6-(1-o-methoxyphenyl-5-methyl-1,2,3-triazol-4-yl)-3-(4-pyridyl)-s-triazolo[3,4-b]-1,3,4-thiadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%	With trichlorophosphate for 6h; Heating;

Reference： [1]Sun, Xiao-Wen; Zhang, Yan; Zhang, Zi-Yi; Wang, Qin; Wang, Shu-Fang [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 3, p. 380 - 383]

13
[ 36209-51-5 ]
[ 31802-54-7 ]
6-(1-p-methoxyphenyl-5-methyl-1,2,3-triazol-4-yl)-3-(4-pyridyl)-s-triazolo[3,4-b]-1,3,4-thiadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With trichlorophosphate for 6h; Heating;

Reference： [1]Sun, Xiao-Wen; Zhang, Yan; Zhang, Zi-Yi; Wang, Qin; Wang, Shu-Fang [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 3, p. 380 - 383]

14
[ 15264-63-8 ]
[ 36209-51-5 ]

Yield	Reaction Conditions	Operation in experiment
70%	With hydrazine hydrate for 0.133333h; microwave irradiation;
	With hydrazine hydrate
	Stage #1: 5-(4-pyridinyl)-1,3,4-oxadiazole-2-thiol With hydrazine hydrate at 20℃; for 2h; Stage #2: for 4h; Reflux; Stage #3: With hydrogenchloride

	With hydrazine hydrate In ethanol Reflux;	Synthesis of 1,2,4-triazole : General procedure (3) General procedure: A mixture of isonicotinic acid hydrazide (1),potassium hydroxide and carbon disulfide in ethanolwas refluxed on a oil bath for 10-12 hr to obtain the compound 5-(pyridine-4-yl)-1,3,4-oxadiazole-2-thiol (2)17. Then compound (2) was refluxed with hydrazine hydrate (99%) in absolute ethanol for 8-9 hr on a oilbath to obtain 4-amino-5-(pyridine-4-yl)-4H-1,2,4-triazole-3-thiol (3)
	With pyridine; hydrazine hydrate at 120℃; for 12h;	12.3 Step 3: Preparation of 4-amino-5-(4-pyridyl)-1 ,2,4-triazole-3-thiol To a solution of 5-(4-pyridyl)-1 ,3,4-oxadiazole-2-thiol (0.8 g) in pyridine (12 ml_) was added hydrazine hydrate (0.66 ml_) and the mixture was heated at 120°C for 12 hours. The reaction mass was diluted with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated to give 4-amino-5-(4-pyridyl)-1 ,2,4-triazole-3-thiol as a yellow solid. NMR (400 MHz, DMSO-de) 14.20 (s, 1 H), 5.87 (s, 2H), 8.04 (d, 2H), 8.76 (d, 2H)

Reference： [1]Joshi; Karnik [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 4, p. 1057 - 1059]
[2]Location in patent: scheme or table Bayrak, Hacer; Demirbas, Ahmet; Demirbas, Neslihan; Karaoglu, Senguel Alpay [European Journal of Medicinal Chemistry, 2009, vol. 44, # 11, p. 4362 - 4366]
[3]Ledeţi, Ionuţ; Bercean, Vasile; Alexa, Anda; Şoica, Codruţa; Şuta, Lenuţa-Maria; Dehelean, Cristina; Trandafirescu, Cristina; Muntean, Delia; Licker, Monica; Fuliaş, Adriana [Journal of Chemistry, 2015, vol. 2015]
[4]Sabale, Prafulla M.; Mehta, Pooja [Indian Journal of Heterocyclic Chemistry, 2013, vol. 23, # 2, p. 149 - 154]
[5]Current Patent Assignee: Syngenta (in: Sinochem Holdings); SINOCHEM HOLDINGS CORPORATION LTD - WO2021/64073, 2021, A1 Location in patent: Page/Page column 88-89

15
[ 75-15-0 ]
[ 54-85-3 ]
[ 36209-51-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: isoniazid With potassium hydroxide In methanol at 0 - 5℃; Stage #2: carbon disulfide In methanol at 0 - 20℃; Stage #3: With hydrazine hydrate In water Reflux;	4.1.1. General method for preparation of 4-amino-5-pyridin-4-yl-4H-[1,2,4]triazole-3-thiol (2) Isonicotinic acid hydrazide (11.37 g, 0.083 mol) was treated witha solution of KOH (6.4 g, 0.125 mol) dissolved in methanol (50 mL) at 0-5 °C with stirring. Carbon disulphide (9.6 g, 0.125 mol) was added slowly and the reaction mixture was stirred over night atroom temperature. The solid product of potassium dithiocarbazinate 1 was filtered, washed with chilled methanol and dried. It was directly used in the next step without further purification. Hydrazine hydrate (9 g, 0.2 mol) was added to a solution of 1(22 g, 0.1 mol) in water (20 mL) and the reaction mixture heated under reflux till complete evolution of H2S. The reaction mixture was poured on ice cold water and acidified with HCl. The yellow precipitate was filtered, washed with cold water, dried and crystallized from ethanol. Yield: 80%; m.p.: 240-242 °C; IR (kBr, cm-1): 3271 (NH2), 3159 (Ar-H), 2881 (CH aliphatic), 2561 (SH), 1608 (C=N); 1H NMR (DMSO-d6): δ 5.87 (s, 2H, NH2, D2O exchangeable), 8.01 (d, 2H, J 6.0 Hz, Pyridine H-3 and H-5), 8.75 (d, 2H, J = 6.0 Hz,Pyridine H-2 and H-6), 14.12 (s, 1H, SH, D2O exchangeable).
72%	Stage #1: carbon disulfide; isoniazid With potassium hydroxide In ethanol at 20℃; for 12h; Stage #2: With hydrazine hydrate In water for 6h; Reflux; Stage #3: With hydrogenchloride In water Cooling;
72%	Stage #1: carbon disulfide; isoniazid With potassium hydroxide In ethanol at 20℃; Stage #2: With hydrazine In water for 6h; Reflux;	1 Intermediate: 4-amino-5- (pyridin-4-yl) -4H-1,2,4-triazole-3-thiol (III) Carbon disulfide (3.3 ml, 5.5 mmol) was added dropwise to a solution of KOH (3.0 g, 5.5 mmol)withPyridinePyridineIsoniazid (3.6 mmol) in ethanol (70 ml).The mixture was stirred at room temperature overnight,Then cooled in an ice-water bath and diluted with diethyl ether.The precipitate was filtered off and washed with diethyl ether and dried.The product (1.6 mmol) was dissolved in water (2 ml)Hydrazine hydrate (2.4 mmol) was added,The mixture was refluxed under stirring for 6 hr.Then, 80 ml of water was added to the reaction mixture and neutralized with concentrated hydrochloric acid. The precipitate was filtered through water and dried. The yield of intermediate III was 72%.1H NMR (200 MHz, DMSO-d6):? [Ppm] =5.86 (s, 2H, -NH2), 8.00-8.03 (d, 2H, 3J = 6.13 Hz, 20, 60-H), 8.74-8.77 (d,2H, 3J = 6.13 Hz, 30, 50-H), 13.89 (s, 1H, -SH).

	Stage #1: carbon disulfide; isoniazid With potassium hydroxide Stage #2: With hydrazine hydrate at 120℃;
	Stage #1: carbon disulfide; isoniazid With potassium hydroxide In ethanol; water for 4.5h; Stage #2: With hydrazine hydrate In water for 8h; Reflux;
	Stage #1: carbon disulfide; isoniazid With potassium hydroxide In ethanol for 4h; Reflux; Stage #2: With hydroxylamine monohydrate In ethanol for 2h; Reflux;
	Stage #1: carbon disulfide; isoniazid With potassium hydroxide In ethanol Stage #2: With hydrazine hydrate
	Stage #1: carbon disulfide; isoniazid With potassium hydroxide In ethanol at 20℃; for 5h; Cooling with ice; Stage #2: With hydrazine hydrate In water Reflux;
	Stage #1: carbon disulfide; isoniazid With potassium hydroxide In ethanol at 20℃; for 16h; Stage #2: In diethyl ether; ethanol for 3h; Stage #3: With hydrazine hydrate In diethyl ether; ethanol; water for 8h; Reflux;
	Stage #1: carbon disulfide; isoniazid With potassium hydroxide In ethanol for 24h; Stage #2: With hydrazine hydrate In water for 0.166667h; Microwave irradiation; Reflux;
	Stage #1: carbon disulfide; isoniazid With potassium hydroxide In ethanol Stage #2: With hydrazine hydrate In ethanol

Reference： [1]Kamel, Mona M.; Megally Abdo, Nadia Y. [European Journal of Medicinal Chemistry, 2014, vol. 86, p. 75 - 80]
[2]Location in patent: experimental part Cheeseright, Timothy J.; Holm, Melanie; Lehmann, Frank; Luik, Sabine; Gottert, Marcia; Melville, James L.; Laufer, Stefan [Journal of Medicinal Chemistry, 2009, vol. 52, # 14, p. 4200 - 4209]
[3]Current Patent Assignee: ZAISHENGYUAN WUXI BIOLOGICAL MEDICINE TECH; FUDAN UNIVERSITY - CN106674251, 2017, A Location in patent: Paragraph 0025-0026
[4]Li, Dejiang; Long, Deqing; Fu, Heqing [Phosphorus, Sulfur and Silicon and the Related Elements, 2006, vol. 181, # 9, p. 2079 - 2087]
[5]Location in patent: experimental part Singh, Ram J.; Singh, Dharmendra K. [South African Journal of Chemistry, 2009, vol. 62, p. 105 - 108]
[6]Location in patent: experimental part Reddy, Vanga Malla; Reddy, Kunduru Ravinder [Chemical and Pharmaceutical Bulletin, 2010, vol. 58, # 8, p. 1081 - 1084]
[7]Location in patent: scheme or table Chen, Xiqing; Liu, Chenjiang; Wang, Jide; Li, Yanping [Journal of Heterocyclic Chemistry, 2010, vol. 47, # 5, p. 1225 - 1229]
[8]Location in patent: experimental part Gilani, Sadaf Jamal; Khan, Suroor Ahmad; Alam, Ozair; Siddiqui, Nadeem [Acta poloniae pharmaceutica, 2011, vol. 68, # 2, p. 205 - 211]
[9]Location in patent: experimental part Mishra, Ravinesh; Kumar, Rajiv; Kumar, Suresh; Majeed, Jaseela; Rashid, Mohd; Sharma, Sameer [Journal of the Chilean Chemical Society, 2010, vol. 55, # 3, p. 359 - 362]
[10]Location in patent: experimental part Bhatia, Manish Sudesh; Zarekar, Bandu Eknath; Choudhari, Prafulla Balkrishna; Ingale, Kundan Bhanudas; Bhatia, Neela Manish [Medicinal Chemistry Research, 2011, vol. 20, # 1, p. 116 - 120]
[11]Vijesh; Isloor, Arun M.; Shetty, Prashanth; Sundershan; Fun, Hoong Kun [European Journal of Medicinal Chemistry, 2013, vol. 62, p. 410 - 415]

16
[ 33603-90-6 ]
[ 36209-51-5 ]
3-(4-pyridyl)-7-(phenylmethylene)-s-triazol[3,4b][1,3,4]-thiadiazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With triethylamine In ethanol for 5h; Heating / reflux;	2 To prepare Compound IIa by one-step preparation, 102 mg (0.53 mmol) of 4-amino-3-(4-pyridyl)-5-mercapto[4H]-1,2,4triazole were refluxed with 740 μL (0.53 mmol) of triethylamine in 25 mL of anhydrous ethanol until complete dissolution. To this solution was added α-bromocinnamaldehyde (197 mg, 0.93 mmol) and the mixture was refluxed for 5 hours. Over time the product precipitated out of solution and, after cooling down the reaction to room temperature, it was isolated by filtration and washed with ethanol. Yellow crystals were obtained after recrystallization from ethanol/DMSO. 92 mg, 57%, mp=245-246° C. Anal. Calcd. for C16H11N5S: C, 62.93%; H, 3.63%; N, 22.93%. Found: C, 62.86%; H, 3.42%; N, 22.86%. 1H NMR (d6-DMSO) δ: 7.47-7.63 (m, 6H, Ph and Hγ); 7.99 (dd, J=1.5 Hz, J'=4.5 Hz, 2H, Hb); 8.23 (s, 1H, Hα); 8.77 (dd, J=1.5 Hz, J'=4.5 Hz, 2H, Ha).

Reference： [1]Current Patent Assignee: RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY - US2006/40926, 2006, A1 Location in patent: Page/Page column 6

17
[ 36209-51-5 ]
C₂₃H₁₉BrNO₂Pol [ No CAS ]
[ 872-35-5 ]
[ 3004-42-0 ]
[ 52431-78-4 ]
[ 141-90-2 ]
[ 86-93-1 ]
[ 15264-63-8 ]
C₂₆H₂₂N₃O₂PolS [ No CAS ]
C₂₇H₂₂N₃O₃PolS [ No CAS ]
C₃₀H₂₄N₅O₂PolS [ No CAS ]
C₃₀H₂₃N₄O₃PolS [ No CAS ]
C₃₁H₂₄N₃O₃PolS [ No CAS ]
C₃₀H₂₅N₆O₂PolS [ No CAS ]
C₃₀H₂₄N₅O₃PolS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; for 20h;Combinatorial reaction / High throughput screening (HTS);	Each resin from Step 3 (50 mg each, 50 mumol) was distributed into 32 fritted syringes (Torvig, 50 mg each, 50), for a total of 64 syringes, and was swelled in NMP (1 mL) for 30 min. The solvent was removed from each syringe by filtration. Solutions of each of the sixteen building blocks listed below (10 mmol each) and DIEA (3.5 mL, 20 mmol) in NMP (10 mL) were prepared. 3 mL of solutions C1-C8 were added to the syringes containing the product incorporating building block A1, and 3 mL of solutions C9-C16 were added to the syringes containing the product incorporating building bock A2. The suspensions were then shaken for 20 h on a Titer Plate Shaker. The reaction mixtures were each filtered and washed 5 times with methylene chloride (5 mL), 3 times with THF (5 mL), three times with THF/H2O (3/1 v/v, 5 mL), and three times with THF (5 mL) and the resins were dried overnight under vacuum.

Reference： [1]Patent: US2006/167057,2006,A1 .Location in patent: Page/Page column 61-63

18
[ 36209-51-5 ]
[ 100-39-0 ]
[ 87693-67-2 ]

Yield	Reaction Conditions	Operation in experiment
73%	With sodium hydroxide In methanol
	With sodium hydroxide In methanol at 20℃; for 0.25h;
	With sodium hydroxide In methanol at 20℃; for 2.5h;	General procedure for the synthesis of 5-(pyridin-4-yl)-3-(alkylsulfanyl)-4H-1,2,4-triazol-4-amine derivatives9, 13-15, and 17-18. General procedure: The 4-amino-5-(4-pyridinyl)-4H-1,2,4-triazole-3-thiol (5) (200 mg, 1.03 mmol) and NaOH(41 mg, 1.02 mmol) were dissolved in MeOH (8 mL); after complete dissolution, the suitable alkyl halidederivative (1.03 mmol) was added dropwise. We generally employed alkyl bromide derivatives to preparedesigned compounds, except for desired compound 9 for which we used the suitable alkyl chloride derivative.The reaction mixture was stirred for 2.5 hours at room temperature. Upon completion of the reaction, thesolvent was removed under reduced pressure and the solid residue was re-crystalized from diethylether/ethanol, providing the pure final pyridyl-triazole derivatives as a powder. The registered CAS number forcompound 9 has been already assigned and is available at https://www.cas.org; however, its syntheticprocedure, chemical and structural characterization are not available in literature.

Reference： [1]Location in patent: experimental part Kolodina; Gaponenko; Lesin [Russian Chemical Bulletin, 2008, vol. 57, # 6, p. 1273 - 1276]
[2]Adornato, Ilenia; De Luca, Laura; Gitto, Rosaria; Ventura, Salvador; Vittorio, Serena; Peña-Díaz, Samuel [Journal of Enzyme Inhibition and Medicinal Chemistry, 2020, vol. 35, # 1, p. 1727 - 1735]
[3]Adornato, lenia; Cacciola, Anna; De Luca, Laura; Germano, Maria Paola; Gitto, Rosaria; Mirabile, Salvatore; Ricci, Federico [Arkivoc, 2022, vol. 2022, # 2, p. 156 - 166]

19
[ 36209-51-5 ]
[ 74-96-4 ]
[ 901096-40-0 ]

Yield	Reaction Conditions	Operation in experiment
74.3%	Stage #1: 4-amino-5-(pyridine-4-yl)-4H-1,2,4-triazole-3-thiol With natrium In ethanol at 20℃; for 0.5h; Stage #2: bromure d'ethyle In ethanol for 4h; Reflux;
	With sodium hydroxide In methanol at 20℃; for 2h;

Reference： [1]Location in patent: experimental part Bayrak, Hacer; Demirbas, Ahmet; Demirbas, Neslihan; Karaoglu, Senguel Alpay [European Journal of Medicinal Chemistry, 2009, vol. 44, # 11, p. 4362 - 4366]
[2]Bucolo, Federica; Cuzzocrea, Salvatore; De Luca, Laura; Di Paola, Rosanna; Gitto, Rosaria; Peña-Díaz, Samuel; Siracusa, Rosalba; Ventura, Salvador; Vittorio, Serena [ACS Chemical Neuroscience, 2022, vol. 13, # 5, p. 581 - 586]

20
[ 36209-51-5 ]
[ 32596-43-3 ]
[ 1094597-77-9 ]

Reference： [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2008,vol. 71,p. 1474 - 1480

21
[ 36209-51-5 ]
[ 73289-61-9 ]
[ 1094597-76-8 ]

Yield	Reaction Conditions	Operation in experiment
64%	With sulfuric acid In ethanol Reflux;

Reference： [1]Location in patent: experimental part Khanmohammadi, Hamid; Abnosi, Mohammad H.; Hosseinzadeh, Ali; Erfantalab, Malihe [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2008, vol. 71, # 4, p. 1474 - 1480]

22
[ 36209-51-5 ]
[ 104-87-0 ]
[ 500144-66-1 ]

Yield	Reaction Conditions	Operation in experiment
88.14%	In N,N-dimethyl-formamide for 0.025h; Microwave irradiation;	Method B - Microwave General procedure: 4-Amino-3-mercapto-5-pyridin-4-yl-4H-1,2,4-triazole (0.965 g, 0.005 mol) was taken in a RB flask, dissolved in minimum amount of DMF (5 mL) and then required amount of respective aryl aldehyde (0.005 mol) added to this solution. The RB flask was kept in a beaker and microwave irradiation was carried out for 1-1.5 min at 900 W until the solution become yellowish in colour. The resulting solution was poured onto crushed ice. The precipitate which got separated was dried and purified by recrystallization from methanol. The homogeneity of the product was checked by melting point and TLC using ethyl acetate methanol (1:1) as developing solvent and iodine vapor as visualizing agent.
71%	With acetic acid for 3h; Reflux;
67%	With sulfuric acid In ethanol Reflux;

Reference： [1]Majumder, Sujan; Bashyal, Bishnu Maya; Gupta [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 10, p. 1260 - 1274]
[2]Location in patent: experimental part Foroughifar, Naser; Mobinikhaledi, Akbar; Ebrahimi, Sattar [Synthetic Communications, 2010, vol. 40, # 16, p. 2421 - 2428]
[3]Location in patent: experimental part Khanmohammadi, Hamid; Abnosi, Mohammad H.; Hosseinzadeh, Ali; Erfantalab, Malihe [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2008, vol. 71, # 4, p. 1474 - 1480]

23
[ 36209-51-5 ]
[ 104-88-1 ]
[ 133847-01-5 ]

Yield	Reaction Conditions	Operation in experiment
75%	With acetic acid for 3h; Reflux;
73%	With sulfuric acid In ethanol Reflux;
69.73%	In N,N-dimethyl-formamide for 0.025h; Microwave irradiation;	Method B - Microwave General procedure: 4-Amino-3-mercapto-5-pyridin-4-yl-4H-1,2,4-triazole (0.965 g, 0.005 mol) was taken in a RB flask, dissolved in minimum amount of DMF (5 mL) and then required amount of respective aryl aldehyde (0.005 mol) added to this solution. The RB flask was kept in a beaker and microwave irradiation was carried out for 1-1.5 min at 900 W until the solution become yellowish in colour. The resulting solution was poured onto crushed ice. The precipitate which got separated was dried and purified by recrystallization from methanol. The homogeneity of the product was checked by melting point and TLC using ethyl acetate methanol (1:1) as developing solvent and iodine vapor as visualizing agent.

58%	In methanol Reflux;	Synthesis of 4-(4-substituted benzylideneamino)-5-(pyridine-4-yl)-4H-1,2,4-triazole-3-thiol (4a-f) : General procedure General procedure: Equimolar quantities of compound (3) (0.001 mol)and p-substituted benzaldehydes (0.001 mol) were dissolved in methanol. The mixture was refluxed on water bath for about 10-14 hr. Progress of the reaction was monitored by TLC. The solution was poured inice cold water and the resulting solid was filtered,washed and recrystallized with suitable solvents viz.methanol, ethanol, acetone and benzene theirphysicochemical data mentioned are in Table-1.
44%	With acetic acid In N,N-dimethyl-formamide for 9h; Reflux;

Reference： [1]Location in patent: experimental part Foroughifar, Naser; Mobinikhaledi, Akbar; Ebrahimi, Sattar [Synthetic Communications, 2010, vol. 40, # 16, p. 2421 - 2428]
[2]Location in patent: experimental part Khanmohammadi, Hamid; Abnosi, Mohammad H.; Hosseinzadeh, Ali; Erfantalab, Malihe [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2008, vol. 71, # 4, p. 1474 - 1480]
[3]Majumder, Sujan; Bashyal, Bishnu Maya; Gupta [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 10, p. 1260 - 1274]
[4]Sabale, Prafulla M.; Mehta, Pooja [Indian Journal of Heterocyclic Chemistry, 2013, vol. 23, # 2, p. 149 - 154]
[5]Location in patent: experimental part Mishra, Ravinesh; Kumar, Rajiv; Kumar, Suresh; Majeed, Jaseela; Rashid, Mohd; Sharma, Sameer [Journal of the Chilean Chemical Society, 2010, vol. 55, # 3, p. 359 - 362]

24
[ 36209-51-5 ]
[ 555-16-8 ]
[ 497864-69-4 ]

Yield	Reaction Conditions	Operation in experiment
92.02%	In N,N-dimethyl-formamide for 0.025h; Microwave irradiation;	Method B - Microwave General procedure: 4-Amino-3-mercapto-5-pyridin-4-yl-4H-1,2,4-triazole (0.965 g, 0.005 mol) was taken in a RB flask, dissolved in minimum amount of DMF (5 mL) and then required amount of respective aryl aldehyde (0.005 mol) added to this solution. The RB flask was kept in a beaker and microwave irradiation was carried out for 1-1.5 min at 900 W until the solution become yellowish in colour. The resulting solution was poured onto crushed ice. The precipitate which got separated was dried and purified by recrystallization from methanol. The homogeneity of the product was checked by melting point and TLC using ethyl acetate methanol (1:1) as developing solvent and iodine vapor as visualizing agent.
85%	With sulfuric acid In ethanol Reflux;
85%	With acetic acid for 3h; Reflux;

79%

In methanol Reflux;

Synthesis of 4-(4-substituted benzylideneamino)-5-(pyridine-4-yl)-4H-1,2,4-triazole-3-thiol (4a-f) : General procedure General procedure: Equimolar quantities of compound (3) (0.001 mol)and p-substituted benzaldehydes (0.001 mol) were dissolved in methanol. The mixture was refluxed on water bath for about 10-14 hr. Progress of the reaction was monitored by TLC. The solution was poured inice cold water and the resulting solid was filtered,washed and recrystallized with suitable solvents viz.methanol, ethanol, acetone and benzene theirphysicochemical data mentioned are in Table-1.

Reference： [1]Majumder, Sujan; Bashyal, Bishnu Maya; Gupta [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 10, p. 1260 - 1274]
[2]Location in patent: experimental part Khanmohammadi, Hamid; Abnosi, Mohammad H.; Hosseinzadeh, Ali; Erfantalab, Malihe [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2008, vol. 71, # 4, p. 1474 - 1480]
[3]Location in patent: experimental part Foroughifar, Naser; Mobinikhaledi, Akbar; Ebrahimi, Sattar [Synthetic Communications, 2010, vol. 40, # 16, p. 2421 - 2428]
[4]Sabale, Prafulla M.; Mehta, Pooja [Indian Journal of Heterocyclic Chemistry, 2013, vol. 23, # 2, p. 149 - 154]

25
[ 36209-51-5 ]
[ 123-11-5 ]
[ 133846-98-7 ]

Yield	Reaction Conditions	Operation in experiment
83.6%	In N,N-dimethyl-formamide for 0.0166667h; Microwave irradiation;	Method B - Microwave General procedure: 4-Amino-3-mercapto-5-pyridin-4-yl-4H-1,2,4-triazole (0.965 g, 0.005 mol) was taken in a RB flask, dissolved in minimum amount of DMF (5 mL) and then required amount of respective aryl aldehyde (0.005 mol) added to this solution. The RB flask was kept in a beaker and microwave irradiation was carried out for 1-1.5 min at 900 W until the solution become yellowish in colour. The resulting solution was poured onto crushed ice. The precipitate which got separated was dried and purified by recrystallization from methanol. The homogeneity of the product was checked by melting point and TLC using ethyl acetate methanol (1:1) as developing solvent and iodine vapor as visualizing agent.
68%	With acetic acid for 3h; Reflux;
65%	With sulfuric acid In ethanol Reflux;

60%	In methanol Reflux;	Synthesis of 4-(4-substituted benzylideneamino)-5-(pyridine-4-yl)-4H-1,2,4-triazole-3-thiol (4a-f) : General procedure General procedure: Equimolar quantities of compound (3) (0.001 mol)and p-substituted benzaldehydes (0.001 mol) were dissolved in methanol. The mixture was refluxed on water bath for about 10-14 hr. Progress of the reaction was monitored by TLC. The solution was poured inice cold water and the resulting solid was filtered,washed and recrystallized with suitable solvents viz.methanol, ethanol, acetone and benzene theirphysicochemical data mentioned are in Table-1.
50.8%	With acetic acid In N,N-dimethyl-formamide for 9h; Reflux;

Reference： [1]Majumder, Sujan; Bashyal, Bishnu Maya; Gupta [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 10, p. 1260 - 1274]
[2]Location in patent: experimental part Foroughifar, Naser; Mobinikhaledi, Akbar; Ebrahimi, Sattar [Synthetic Communications, 2010, vol. 40, # 16, p. 2421 - 2428]
[3]Location in patent: experimental part Khanmohammadi, Hamid; Abnosi, Mohammad H.; Hosseinzadeh, Ali; Erfantalab, Malihe [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2008, vol. 71, # 4, p. 1474 - 1480]
[4]Sabale, Prafulla M.; Mehta, Pooja [Indian Journal of Heterocyclic Chemistry, 2013, vol. 23, # 2, p. 149 - 154]
[5]Location in patent: experimental part Mishra, Ravinesh; Kumar, Rajiv; Kumar, Suresh; Majeed, Jaseela; Rashid, Mohd; Sharma, Sameer [Journal of the Chilean Chemical Society, 2010, vol. 55, # 3, p. 359 - 362]

26
[ 36209-51-5 ]
[ 90-02-8 ]
[ 500196-83-8 ]

Yield	Reaction Conditions	Operation in experiment
87.54%	In N,N-dimethyl-formamide for 0.025h; Microwave irradiation;	Method B - Microwave General procedure: 4-Amino-3-mercapto-5-pyridin-4-yl-4H-1,2,4-triazole (0.965 g, 0.005 mol) was taken in a RB flask, dissolved in minimum amount of DMF (5 mL) and then required amount of respective aryl aldehyde (0.005 mol) added to this solution. The RB flask was kept in a beaker and microwave irradiation was carried out for 1-1.5 min at 900 W until the solution become yellowish in colour. The resulting solution was poured onto crushed ice. The precipitate which got separated was dried and purified by recrystallization from methanol. The homogeneity of the product was checked by melting point and TLC using ethyl acetate methanol (1:1) as developing solvent and iodine vapor as visualizing agent.
83%	With sulfuric acid In ethanol Reflux;

Reference： [1]Majumder, Sujan; Bashyal, Bishnu Maya; Gupta [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 10, p. 1260 - 1274]
[2]Location in patent: experimental part Khanmohammadi, Hamid; Abnosi, Mohammad H.; Hosseinzadeh, Ali; Erfantalab, Malihe [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2008, vol. 71, # 4, p. 1474 - 1480]

27
[ 36209-51-5 ]
[ 874-42-0 ]
[ 488102-67-6 ]

Yield	Reaction Conditions	Operation in experiment
80%	In N,N-dimethyl-formamide for 0.0166667h; Microwave irradiation;	Method B - Microwave General procedure: 4-Amino-3-mercapto-5-pyridin-4-yl-4H-1,2,4-triazole (0.965 g, 0.005 mol) was taken in a RB flask, dissolved in minimum amount of DMF (5 mL) and then required amount of respective aryl aldehyde (0.005 mol) added to this solution. The RB flask was kept in a beaker and microwave irradiation was carried out for 1-1.5 min at 900 W until the solution become yellowish in colour. The resulting solution was poured onto crushed ice. The precipitate which got separated was dried and purified by recrystallization from methanol. The homogeneity of the product was checked by melting point and TLC using ethyl acetate methanol (1:1) as developing solvent and iodine vapor as visualizing agent.
76%	With sulfuric acid In ethanol Reflux;

Reference： [1]Majumder, Sujan; Bashyal, Bishnu Maya; Gupta [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 10, p. 1260 - 1274]
[2]Location in patent: experimental part Khanmohammadi, Hamid; Abnosi, Mohammad H.; Hosseinzadeh, Ali; Erfantalab, Malihe [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2008, vol. 71, # 4, p. 1474 - 1480]

28
[ 36209-51-5 ]
[ 122-88-3 ]
[ 133847-09-3 ]

Reference： [1]RSC Advances,2015,vol. 5,p. 97089 - 97101
[2]South African Journal of Chemistry,2009,vol. 62,p. 105 - 108
[3]Journal of the Chemical Society of Pakistan,2010,vol. 32,p. 235 - 239

29
[ 36209-51-5 ]
[ 50-84-0 ]
[ 478362-75-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	With trichlorophosphate for 1.5h; Reflux;
85%	With trichlorophosphate for 1.5h; Reflux;
84%	With trichlorophosphate Reflux;	4.1.3. General method for the preparation of compounds 4a-d General procedure: An equimolar mixture (0.01 mol) of 4-amino-5-pyridin-4-yl-4H-[1,2,4]triazole-3-thiol (2) and the appropriate aromatic acid in POCl3 (10 mL) was refluxed for 8-10 h. The reaction mixture was cooled to room temperature and gradually poured onto ice cold water with stirring. The mixture was allowed to stand overnight and the solid separated out was filtered, treated with dilute NaOH solution and washed thoroughly with cold water. The solid obtained was filtered, dried and crystallized from ethanol.

76%	With trichlorophosphate for 5h; Reflux;
	With trichlorophosphate for 5h; Reflux;

Reference： [1]Location in patent: experimental part Singh, Ram J.; Singh, Dharmendra K. [South African Journal of Chemistry, 2009, vol. 62, p. 105 - 108]
[2]Location in patent: experimental part Singh, Ram Janam; Singh, Dharmendra Kumar [Journal of the Chemical Society of Pakistan, 2010, vol. 32, # 2, p. 235 - 239]
[3]Kamel, Mona M.; Megally Abdo, Nadia Y. [European Journal of Medicinal Chemistry, 2014, vol. 86, p. 75 - 80]
[4]Location in patent: experimental part Gilani, Sadaf Jamal; Khan, Suroor Ahmad; Alam, Ozair; Siddiqui, Nadeem [Acta poloniae pharmaceutica, 2011, vol. 68, # 2, p. 205 - 211]
[5]Location in patent: experimental part Gilani, Sadaf J.; Khan, Suroor A.; Siddiqui, Nadeem [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 16, p. 4762 - 4765]

30
[ 36209-51-5 ]
[ 2976-75-2 ]
[ 478363-06-3 ]

Yield	Reaction Conditions	Operation in experiment
87%	With trichlorophosphate for 1.5h; Reflux;
87%	With trichlorophosphate for 1.5h; Reflux;

Reference： [1]Location in patent: experimental part Singh, Ram J.; Singh, Dharmendra K. [South African Journal of Chemistry, 2009, vol. 62, p. 105 - 108]
[2]Location in patent: experimental part Singh, Ram Janam; Singh, Dharmendra Kumar [Journal of the Chemical Society of Pakistan, 2010, vol. 32, # 2, p. 235 - 239]

31
[ 36209-51-5 ]
[ 1878-49-5 ]
[ 478363-00-7 ]

Yield	Reaction Conditions	Operation in experiment
75%	With trichlorophosphate;Reflux;	General procedure: A mixture of 4-amino-5-(pyridin-3-yl)-4H-[1,2,4]triazole-3-thiol 3 (1 mmol) and substituted aromatic acids (1.1 mmol) inPOCl3 (5 mL) was refluxed for 6-7 h. The reaction mixture was slowly poured into crushed ice with stirring and neutralized with sodium bicarbonate. Solid material was filtered, washed with cold water, dried, and recrystallized from ethanol to afford 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles 4a-g and 5a-e [25].

Reference： [1]South African Journal of Chemistry,2009,vol. 62,p. 105 - 108
[2]Journal of the Chemical Society of Pakistan,2010,vol. 32,p. 235 - 239
[3]European Journal of Medicinal Chemistry,2014,vol. 78,p. 167 - 177

32
[ 36209-51-5 ]
[ 65-85-0 ]
[ 133847-07-1 ]

Yield	Reaction Conditions	Operation in experiment
90%	With trichlorophosphate for 1.5h; Reflux;
90%	With trichlorophosphate for 1.5h; Reflux;
78%	With trichlorophosphate for 5h; Reflux;

70%	With trichlorophosphate for 8h; Reflux;	Synthesis of 6-phenyl-3-(4-pyridyl)-1,2,4-triazolo-[3,4-b][1,3,4]thiadiazole (II) To a mixture of 4-amino-5-(4-pyridyl)-4H-1,2,4-triazole-3-thiol, (I) (5 mmol, 0.965 g.) and benzoic acid (1 mmol, 0.61 g.) phosphorous oxychloride (27 mmol, 2.5 ml) was added and the resulting mixture heated under reflux for 8 h in a water bath. The excess phosphorous oxychloride was then distilled of and the residue was poured onto crushed ice while stirring. The resulting solid was washed with dilute sodium bicarbonate solution and then recrystallized from dimethylformamide. Yield 70%; m.p. 222-224 °C; IR ν (cm-1): 3102-3011 (Ar-CH), 1601-1592 (C=C, C=N), 665 (C-S-C). 1H NMR(400 MHz, DMSO-d6, ppm): δ 8.07 (d, J = 7.03, 2H, o-Ar-CH), 7.62-7.69 (m, 3H, m, p-Ar-CH), 8.24 (dd, 2H, J = 6.23, 1.47, pyridine C-CH), 8.82 (d, J = 5.87, 2H, pyridine N-CH). 13C NMR (100 MHz, DMSO-d6, ppm): 168.36, 151.46, 144.39, 133.69, 133.07, 130.43, 130.20, 129.50, 128.08, 120.16.
60%	With trichlorophosphate for 5h; Reflux;
55%	With trichlorophosphate Reflux;	4.1.3. General method for the preparation of compounds 4a-d General procedure: An equimolar mixture (0.01 mol) of 4-amino-5-pyridin-4-yl-4H-[1,2,4]triazole-3-thiol (2) and the appropriate aromatic acid in POCl3 (10 mL) was refluxed for 8-10 h. The reaction mixture was cooled to room temperature and gradually poured onto ice cold water with stirring. The mixture was allowed to stand overnight and the solid separated out was filtered, treated with dilute NaOH solution and washed thoroughly with cold water. The solid obtained was filtered, dried and crystallized from ethanol.
53%	With trichlorophosphate Reflux;
50%	With trichlorophosphate at 120℃; for 8h;
	With trichlorophosphate for 5h; Reflux;

Reference： [1]Location in patent: experimental part Singh, Ram J.; Singh, Dharmendra K. [South African Journal of Chemistry, 2009, vol. 62, p. 105 - 108]
[2]Location in patent: experimental part Singh, Ram Janam; Singh, Dharmendra Kumar [Journal of the Chemical Society of Pakistan, 2010, vol. 32, # 2, p. 235 - 239]
[3]Location in patent: experimental part Gilani, Sadaf Jamal; Khan, Suroor Ahmad; Alam, Ozair; Siddiqui, Nadeem [Acta poloniae pharmaceutica, 2011, vol. 68, # 2, p. 205 - 211]
[4]Cansiz, Ahmet; Cetin, Ahmet; Orek, Cahit; Karatepe, Mustafa; Sarac, Kamiran; Kus, Alper; Koparir, Pelin [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2012, vol. 97, p. 606 - 615]
[5]Location in patent: experimental part Hussein, Mostafa A.; Shaker, Refaat M.; Ameen, Mohammed A.; Mohammed, Mohammed F. [Archives of Pharmacal Research, 2011, vol. 34, # 8, p. 1239 - 1250]
[6]Kamel, Mona M.; Megally Abdo, Nadia Y. [European Journal of Medicinal Chemistry, 2014, vol. 86, p. 75 - 80]
[7]Location in patent: experimental part Mobinikhaledi, Akbar; Foroughifar, Naser; Bayat, Mahsa [Organic Preparations and Procedures International, 2011, vol. 43, # 4, p. 368 - 371]
[8]Fan, Jian-Zhong; Li, Jin-Ping; Zhang, Li-Peng; Zhang, Liu-Gen; Wang, Duo-Zhi [Journal of the Chinese Chemical Society, 2015, vol. 62, # 9, p. 786 - 792]
[9]Location in patent: experimental part Gilani, Sadaf J.; Khan, Suroor A.; Siddiqui, Nadeem [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 16, p. 4762 - 4765]

33
[ 36209-51-5 ]
[ 118-91-2 ]
[ 136025-39-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	With trichlorophosphate for 1.5h; Reflux;
82%	With trichlorophosphate for 5h; Reflux;
75%	With trichlorophosphate Reflux;	4.1.3. General method for the preparation of compounds 4a-d General procedure: An equimolar mixture (0.01 mol) of 4-amino-5-pyridin-4-yl-4H-[1,2,4]triazole-3-thiol (2) and the appropriate aromatic acid in POCl3 (10 mL) was refluxed for 8-10 h. The reaction mixture was cooled to room temperature and gradually poured onto ice cold water with stirring. The mixture was allowed to stand overnight and the solid separated out was filtered, treated with dilute NaOH solution and washed thoroughly with cold water. The solid obtained was filtered, dried and crystallized from ethanol.

55%	With trichlorophosphate Reflux;
	With trichlorophosphate for 5h; Reflux;

Reference： [1]Location in patent: experimental part Singh, Ram J.; Singh, Dharmendra K. [South African Journal of Chemistry, 2009, vol. 62, p. 105 - 108]
[2]Location in patent: experimental part Gilani, Sadaf Jamal; Khan, Suroor Ahmad; Alam, Ozair; Siddiqui, Nadeem [Acta poloniae pharmaceutica, 2011, vol. 68, # 2, p. 205 - 211]
[3]Kamel, Mona M.; Megally Abdo, Nadia Y. [European Journal of Medicinal Chemistry, 2014, vol. 86, p. 75 - 80]
[4]Location in patent: experimental part Mobinikhaledi, Akbar; Foroughifar, Naser; Bayat, Mahsa [Organic Preparations and Procedures International, 2011, vol. 43, # 4, p. 368 - 371]
[5]Location in patent: experimental part Gilani, Sadaf J.; Khan, Suroor A.; Siddiqui, Nadeem [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 16, p. 4762 - 4765]

34
[ 36209-51-5 ]
[ 3132-99-8 ]
[ 488088-39-7 ]

Yield	Reaction Conditions	Operation in experiment
77.78%	In N,N-dimethyl-formamide for 0.0166667h; Microwave irradiation;	Method B - Microwave General procedure: 4-Amino-3-mercapto-5-pyridin-4-yl-4H-1,2,4-triazole (0.965 g, 0.005 mol) was taken in a RB flask, dissolved in minimum amount of DMF (5 mL) and then required amount of respective aryl aldehyde (0.005 mol) added to this solution. The RB flask was kept in a beaker and microwave irradiation was carried out for 1-1.5 min at 900 W until the solution become yellowish in colour. The resulting solution was poured onto crushed ice. The precipitate which got separated was dried and purified by recrystallization from methanol. The homogeneity of the product was checked by melting point and TLC using ethyl acetate methanol (1:1) as developing solvent and iodine vapor as visualizing agent.
58%	With acetic acid for 3h; Reflux;

Reference： [1]Majumder, Sujan; Bashyal, Bishnu Maya; Gupta [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 10, p. 1260 - 1274]
[2]Location in patent: experimental part Foroughifar, Naser; Mobinikhaledi, Akbar; Ebrahimi, Sattar [Synthetic Communications, 2010, vol. 40, # 16, p. 2421 - 2428]

35
[ 36209-51-5 ]
[ 89-98-5 ]
[ 354131-52-5 ]

Yield	Reaction Conditions	Operation in experiment
76.07%	In N,N-dimethyl-formamide for 0.0166667h; Microwave irradiation;	Method B - Microwave General procedure: 4-Amino-3-mercapto-5-pyridin-4-yl-4H-1,2,4-triazole (0.965 g, 0.005 mol) was taken in a RB flask, dissolved in minimum amount of DMF (5 mL) and then required amount of respective aryl aldehyde (0.005 mol) added to this solution. The RB flask was kept in a beaker and microwave irradiation was carried out for 1-1.5 min at 900 W until the solution become yellowish in colour. The resulting solution was poured onto crushed ice. The precipitate which got separated was dried and purified by recrystallization from methanol. The homogeneity of the product was checked by melting point and TLC using ethyl acetate methanol (1:1) as developing solvent and iodine vapor as visualizing agent.
60%	With acetic acid for 3h; Reflux;

Reference： [1]Majumder, Sujan; Bashyal, Bishnu Maya; Gupta [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 10, p. 1260 - 1274]
[2]Location in patent: experimental part Foroughifar, Naser; Mobinikhaledi, Akbar; Ebrahimi, Sattar [Synthetic Communications, 2010, vol. 40, # 16, p. 2421 - 2428]

36
[ 36209-51-5 ]
[ 552-89-6 ]
[ 497231-69-3 ]

Yield	Reaction Conditions	Operation in experiment
92.02%	In N,N-dimethyl-formamide for 0.0166667h; Microwave irradiation;	Method B - Microwave General procedure: 4-Amino-3-mercapto-5-pyridin-4-yl-4H-1,2,4-triazole (0.965 g, 0.005 mol) was taken in a RB flask, dissolved in minimum amount of DMF (5 mL) and then required amount of respective aryl aldehyde (0.005 mol) added to this solution. The RB flask was kept in a beaker and microwave irradiation was carried out for 1-1.5 min at 900 W until the solution become yellowish in colour. The resulting solution was poured onto crushed ice. The precipitate which got separated was dried and purified by recrystallization from methanol. The homogeneity of the product was checked by melting point and TLC using ethyl acetate methanol (1:1) as developing solvent and iodine vapor as visualizing agent.
85%	With acetic acid for 3h; Reflux;

Reference： [1]Majumder, Sujan; Bashyal, Bishnu Maya; Gupta [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 10, p. 1260 - 1274]
[2]Location in patent: experimental part Foroughifar, Naser; Mobinikhaledi, Akbar; Ebrahimi, Sattar [Synthetic Communications, 2010, vol. 40, # 16, p. 2421 - 2428]

37
[ 36209-51-5 ]
[ 74-11-3 ]
[ 135586-40-2 ]

Yield	Reaction Conditions	Operation in experiment
82%	With trichlorophosphate Reflux;	4.1.3. General method for the preparation of compounds 4a-d General procedure: An equimolar mixture (0.01 mol) of 4-amino-5-pyridin-4-yl-4H-[1,2,4]triazole-3-thiol (2) and the appropriate aromatic acid in POCl3 (10 mL) was refluxed for 8-10 h. The reaction mixture was cooled to room temperature and gradually poured onto ice cold water with stirring. The mixture was allowed to stand overnight and the solid separated out was filtered, treated with dilute NaOH solution and washed thoroughly with cold water. The solid obtained was filtered, dried and crystallized from ethanol.
60%	With trichlorophosphate Reflux;

Reference： [1]Kamel, Mona M.; Megally Abdo, Nadia Y. [European Journal of Medicinal Chemistry, 2014, vol. 86, p. 75 - 80]
[2]Location in patent: experimental part Mobinikhaledi, Akbar; Foroughifar, Naser; Bayat, Mahsa [Organic Preparations and Procedures International, 2011, vol. 43, # 4, p. 368 - 371]

38
[ 36209-51-5 ]
[ 99-61-6 ]
[ 488136-80-7 ]

Yield	Reaction Conditions	Operation in experiment
79.75%	In N,N-dimethyl-formamide for 0.025h; Microwave irradiation;	Method B - Microwave General procedure: 4-Amino-3-mercapto-5-pyridin-4-yl-4H-1,2,4-triazole (0.965 g, 0.005 mol) was taken in a RB flask, dissolved in minimum amount of DMF (5 mL) and then required amount of respective aryl aldehyde (0.005 mol) added to this solution. The RB flask was kept in a beaker and microwave irradiation was carried out for 1-1.5 min at 900 W until the solution become yellowish in colour. The resulting solution was poured onto crushed ice. The precipitate which got separated was dried and purified by recrystallization from methanol. The homogeneity of the product was checked by melting point and TLC using ethyl acetate methanol (1:1) as developing solvent and iodine vapor as visualizing agent.
66%	With acetic acid In N,N-dimethyl-formamide for 9h; Reflux;

Reference： [1]Majumder, Sujan; Bashyal, Bishnu Maya; Gupta [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 10, p. 1260 - 1274]
[2]Location in patent: experimental part Mishra, Ravinesh; Kumar, Rajiv; Kumar, Suresh; Majeed, Jaseela; Rashid, Mohd; Sharma, Sameer [Journal of the Chilean Chemical Society, 2010, vol. 55, # 3, p. 359 - 362]

39
[ 36209-51-5 ]
[ 587-04-2 ]
[ 498571-06-5 ]

Yield	Reaction Conditions	Operation in experiment
82.41%	In N,N-dimethyl-formamide for 0.0166667h; Microwave irradiation;	Method B - Microwave General procedure: 4-Amino-3-mercapto-5-pyridin-4-yl-4H-1,2,4-triazole (0.965 g, 0.005 mol) was taken in a RB flask, dissolved in minimum amount of DMF (5 mL) and then required amount of respective aryl aldehyde (0.005 mol) added to this solution. The RB flask was kept in a beaker and microwave irradiation was carried out for 1-1.5 min at 900 W until the solution become yellowish in colour. The resulting solution was poured onto crushed ice. The precipitate which got separated was dried and purified by recrystallization from methanol. The homogeneity of the product was checked by melting point and TLC using ethyl acetate methanol (1:1) as developing solvent and iodine vapor as visualizing agent.
51%	With acetic acid In N,N-dimethyl-formamide for 9h; Reflux;

Reference： [1]Majumder, Sujan; Bashyal, Bishnu Maya; Gupta [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 10, p. 1260 - 1274]
[2]Location in patent: experimental part Mishra, Ravinesh; Kumar, Rajiv; Kumar, Suresh; Majeed, Jaseela; Rashid, Mohd; Sharma, Sameer [Journal of the Chilean Chemical Society, 2010, vol. 55, # 3, p. 359 - 362]

40
[ 36209-51-5 ]
[ 100-83-4 ]
[ 497942-65-1 ]

Yield	Reaction Conditions	Operation in experiment
94.28%	In N,N-dimethyl-formamide for 0.025h; Microwave irradiation;	Method B - Microwave General procedure: 4-Amino-3-mercapto-5-pyridin-4-yl-4H-1,2,4-triazole (0.965 g, 0.005 mol) was taken in a RB flask, dissolved in minimum amount of DMF (5 mL) and then required amount of respective aryl aldehyde (0.005 mol) added to this solution. The RB flask was kept in a beaker and microwave irradiation was carried out for 1-1.5 min at 900 W until the solution become yellowish in colour. The resulting solution was poured onto crushed ice. The precipitate which got separated was dried and purified by recrystallization from methanol. The homogeneity of the product was checked by melting point and TLC using ethyl acetate methanol (1:1) as developing solvent and iodine vapor as visualizing agent.
62%	With acetic acid In N,N-dimethyl-formamide for 9h; Reflux;

Reference： [1]Majumder, Sujan; Bashyal, Bishnu Maya; Gupta [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 10, p. 1260 - 1274]
[2]Location in patent: experimental part Mishra, Ravinesh; Kumar, Rajiv; Kumar, Suresh; Majeed, Jaseela; Rashid, Mohd; Sharma, Sameer [Journal of the Chilean Chemical Society, 2010, vol. 55, # 3, p. 359 - 362]

41
[ 36209-51-5 ]
[ 100-10-7 ]
[ 488842-36-0 ]

Yield	Reaction Conditions	Operation in experiment
80.25%	In N,N-dimethyl-formamide for 0.0166667h; Microwave irradiation;	Method B - Microwave General procedure: 4-Amino-3-mercapto-5-pyridin-4-yl-4H-1,2,4-triazole (0.965 g, 0.005 mol) was taken in a RB flask, dissolved in minimum amount of DMF (5 mL) and then required amount of respective aryl aldehyde (0.005 mol) added to this solution. The RB flask was kept in a beaker and microwave irradiation was carried out for 1-1.5 min at 900 W until the solution become yellowish in colour. The resulting solution was poured onto crushed ice. The precipitate which got separated was dried and purified by recrystallization from methanol. The homogeneity of the product was checked by melting point and TLC using ethyl acetate methanol (1:1) as developing solvent and iodine vapor as visualizing agent.
31%	With acetic acid In N,N-dimethyl-formamide for 9h; Reflux;

Reference： [1]Majumder, Sujan; Bashyal, Bishnu Maya; Gupta [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 10, p. 1260 - 1274]
[2]Location in patent: experimental part Mishra, Ravinesh; Kumar, Rajiv; Kumar, Suresh; Majeed, Jaseela; Rashid, Mohd; Sharma, Sameer [Journal of the Chilean Chemical Society, 2010, vol. 55, # 3, p. 359 - 362]

42
[ 36209-51-5 ]
[ 403-29-2 ]
[ 785787-83-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	In ethanol at 95℃; for 0.5h; Microwave irradiation;	1 5.3. Synthetic procedure and analytical data of 3,6-disubstituted triazolothiadiazines (6a-g) General procedure: A mixture of 5a (0.05 g, 0.26 mmol) and 2-bromoacetophenone (0.057 g, 0.29 mmol) were dissolved in absolute alcohol (2.5 mL), and the resulting mixture was heated at 95 °C in the microwave for 30 min. The mixture was allowed to stand overnight, separated solid was filtered, washed thoroughly with cold alcohol and ether, and dried to obtain 6a-1 (0.071 g, 93% yield) as a white solid: mp 226-227 °C
80%	Stage #1: 4-amino-5-(pyridin-4-yl)-4H-1,2,4-triazole-3-thiol; 2-bromo-4'-fluoroacetophenone In ethanol for 2h; Reflux; Stage #2: With ammonium hydroxide In ethanol at 20℃;

Reference： [1]Li, Ziqiang; Bai, Xiaoguang; Deng, Qi; Zhang, Guoning; Zhou, Lei; Liu, Yishuang; Wang, Juxian; Wang, Yucheng [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 1, p. 213 - 220]
[2]Location in patent: experimental part Hussein, Mostafa A.; Shaker, Refaat M.; Ameen, Mohammed A.; Mohammed, Mohammed F. [Archives of Pharmacal Research, 2011, vol. 34, # 8, p. 1239 - 1250]

43
[ 36209-51-5 ]
3-[4-(methylsulfanyl)phenyl]-1H-pyrazole-4-carbaldehyde [ No CAS ]
[ 1430812-52-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid In ethanol for 8h; Reflux;	6.2 General procedure for the synthesis of 4-[(E)-{4-[aryl]-1H-pyrazol-3-yl}methylidene] amino}-5-(substituted)-4H-1,2,4-triazole-3-thiol (11a-d) General procedure: An equimolar mixture of 3-aryl-1H-pyrazole-4-carbaldehyde, 10a-d (0.1 mol) and 4-amino-5-substituted-4H-1,2,4-triazole-3-thiol, 3a-d (0.1 mol) were dissolved in warm ethanol (20 mL). A catalytic amount of sulphuric acid was added to the reaction mixture and refluxed for 8 h, then kept at room temperature overnight. The resultant solid was filtered, washed with chilled ethanol, dried and recrystallized from ethanol-dioxane (1:2) mixture to afford compounds 3a-d.

Reference： [1]Vijesh; Isloor, Arun M.; Shetty, Prashanth; Sundershan; Fun, Hoong Kun [European Journal of Medicinal Chemistry, 2013, vol. 62, p. 410 - 415]

44
[ 36209-51-5 ]
cadmium(II) nitrate tetrhydrate [ No CAS ]
[ 7732-18-5 ]
C₇H₅N₅S^(2-)*C₇H₄N₄S^(2-)*Cd⁽²⁺⁾*H₂O*2H⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	In N,N-dimethyl-formamide at 100℃; for 72h; Autoclave;	2.2.1. Synthesis of 1 A mixture of Cd(NO3)2*4H2O (9.3 mg, 0.03 mM), a-Hptt (11.6 mg, 0.06 mM), DMF (3 mL), and distilled water (5 mL) was sealed in a Teflon-lined stainless-steel autoclave. The mixture was heated at 100 °C for three days and then cooled to room temperature at 5 °C/h; pale yellow block-shaped crystals of 1 were obtained. Yield: 62%. Anal. Calcd (%) for 1: C, 33.84; H, 2.03; N, 25.37. Found: C, 33.42; H,2.33; N, 26.03. IR (KBr, cm-1): 1610.89(s), 1541.74(w), 1467.12(w), 1415.45(s), 1377.69(s), 1222.42(m), 1160.82(m), 1087.49(w), 1061.53(w), 1009.87(m), 962.41(w), 831.83(m),714.73(m), 698.81(m), 688.69(m), 602.70(w), 519.90(w).

Reference： [1]Li, Linke; Li, Wenju; Yang, Sisi; Wei, Lulu; Wang, Changhong; Hou, Hongwei [Journal of Coordination Chemistry, 2013, vol. 66, # 16, p. 2948 - 2956]

45
[ 36209-51-5 ]
[ 626-15-3 ]
[ 1586813-35-5 ]

Yield	Reaction Conditions	Operation in experiment
81%	With potassium hydroxide In ethanol for 1h; Reflux;
	With potassium hydroxide In ethanol; water for 1h; Reflux;	Synthesis of 1,3-bis(4-amino-3-(4-pyridyl)-5-thiomethyl-1,2,4-triazole)benzene (L2) To a solution of 4-amino-3-(4-pyridyl)-5-mercapto-1,2,4-triazole (2 mmol) in aqueous ethanol (50 ml) containing KOH(2 mmol)was added 1,3-bromomethylbenzene (1 mmol). The reaction mixturewas heated under reflux for 1 h. The solvent was removed invacuo and the remaining solid was collected and washed withwater (see Supporting information). 1H NMR(d6-DMSO, ppm):4.46(s, 4H), 6.23(s, 4H), 7.29(m, 3H), 7.56(s, br, 1H), 7.98(dd, 4H,J = 6.00 Hz), 8.72(dd, 4H, J = 6.00 Hz). IR (KBr, cm1); 3334 and3267(NH2), 1602 (CC, CN), 1464, 1556 (CCAN), 1105 (NAN).Anal. Calcd. for C22H20N10S2: C, 54.08; H, 4.13; N, 28.67; S, 13.13.Found: C, 54.2; H, 3.7; N, 28.3; S, 13.3.

Reference： [1]Khanmohammadi, Hamid; Erfantalab, Malihe; Reijerse, Edward J. [Journal of the Iranian Chemical Society, 2014, vol. 11, # 2, p. 323 - 333]
[2]Erfantalab, Malihe; Khanmohammadi, Hamid [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2014, vol. 125, p. 345 - 352]

46
[ 36209-51-5 ]
[ 446-30-0 ]
[ 1190276-99-3 ]

Yield	Reaction Conditions	Operation in experiment
76%	With trichlorophosphate;Reflux;	General procedure: A mixture of 4-amino-5-(pyridin-3-yl)-4H-[1,2,4]triazole-3-thiol 3 (1 mmol) and substituted aromatic acids (1.1 mmol) inPOCl3 (5 mL) was refluxed for 6-7 h. The reaction mixture was slowly poured into crushed ice with stirring and neutralized with sodium bicarbonate. Solid material was filtered, washed with cold water, dried, and recrystallized from ethanol to afford 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles 4a-g and 5a-e [25].

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 78,p. 167 - 177

47
[ 36209-51-5 ]
[ 403-16-7 ]
[ 951962-05-3 ]

Yield	Reaction Conditions	Operation in experiment
78%	With trichlorophosphate;Reflux;	General procedure: A mixture of 4-amino-5-(pyridin-3-yl)-4H-[1,2,4]triazole-3-thiol 3 (1 mmol) and substituted aromatic acids (1.1 mmol) inPOCl3 (5 mL) was refluxed for 6-7 h. The reaction mixture was slowly poured into crushed ice with stirring and neutralized with sodium bicarbonate. Solid material was filtered, washed with cold water, dried, and recrystallized from ethanol to afford 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles 4a-g and 5a-e [25].

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 78,p. 167 - 177

48
[ 88-14-2 ]
[ 36209-51-5 ]
[ 143700-71-4 ]

Yield	Reaction Conditions	Operation in experiment
75%	With trichlorophosphate Reflux;	4.3. Preparation of 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles (4a-g) and (5a-e) General procedure: A mixture of 4-amino-5-(pyridin-3-yl)-4H-[1,2,4]triazole-3-thiol 3 (1 mmol) and substituted aromatic acids (1.1 mmol) inPOCl3 (5 mL) was refluxed for 6-7 h. The reaction mixture was slowly poured into crushed ice with stirring and neutralized with sodium bicarbonate. Solid material was filtered, washed with cold water, dried, and recrystallized from ethanol to afford 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles 4a-g and 5a-e [25].

Reference： [1]Khan, Imtiaz; Zaib, Sumera; Ibrar, Aliya; Rama, Nasim Hasan; Simpson, Jim; Iqbal, Jamshed [European Journal of Medicinal Chemistry, 2014, vol. 78, p. 167 - 177]

49
[ 488-93-7 ]
[ 36209-51-5 ]
[ 1607018-28-9 ]

Yield	Reaction Conditions	Operation in experiment
79%	With trichlorophosphate Reflux;	4.3. Preparation of 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles (4a-g) and (5a-e) General procedure: A mixture of 4-amino-5-(pyridin-3-yl)-4H-[1,2,4]triazole-3-thiol 3 (1 mmol) and substituted aromatic acids (1.1 mmol) inPOCl3 (5 mL) was refluxed for 6-7 h. The reaction mixture was slowly poured into crushed ice with stirring and neutralized with sodium bicarbonate. Solid material was filtered, washed with cold water, dried, and recrystallized from ethanol to afford 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles 4a-g and 5a-e [25].

Reference： [1]Khan, Imtiaz; Zaib, Sumera; Ibrar, Aliya; Rama, Nasim Hasan; Simpson, Jim; Iqbal, Jamshed [European Journal of Medicinal Chemistry, 2014, vol. 78, p. 167 - 177]

50
[ 36209-51-5 ]
[ 6947-94-0 ]
[ 1282102-35-5 ]

Yield	Reaction Conditions	Operation in experiment
77%	With trichlorophosphate Reflux;	4.3. Preparation of 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles (4a-g) and (5a-e) General procedure: A mixture of 4-amino-5-(pyridin-3-yl)-4H-[1,2,4]triazole-3-thiol 3 (1 mmol) and substituted aromatic acids (1.1 mmol) inPOCl3 (5 mL) was refluxed for 6-7 h. The reaction mixture was slowly poured into crushed ice with stirring and neutralized with sodium bicarbonate. Solid material was filtered, washed with cold water, dried, and recrystallized from ethanol to afford 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles 4a-g and 5a-e [25].

Reference： [1]Khan, Imtiaz; Zaib, Sumera; Ibrar, Aliya; Rama, Nasim Hasan; Simpson, Jim; Iqbal, Jamshed [European Journal of Medicinal Chemistry, 2014, vol. 78, p. 167 - 177]

51
[ 36209-51-5 ]
[ 110877-64-0 ]
[ 1607018-29-0 ]

Yield	Reaction Conditions	Operation in experiment
74%	With trichlorophosphate;Reflux;	General procedure: A mixture of 4-amino-5-(pyridin-3-yl)-4H-[1,2,4]triazole-3-thiol 3 (1 mmol) and substituted aromatic acids (1.1 mmol) inPOCl3 (5 mL) was refluxed for 6-7 h. The reaction mixture was slowly poured into crushed ice with stirring and neutralized with sodium bicarbonate. Solid material was filtered, washed with cold water, dried, and recrystallized from ethanol to afford 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles 4a-g and 5a-e [25].

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 78,p. 167 - 177

52
[ 4919-33-9 ]
[ 36209-51-5 ]
[ 1607018-31-4 ]

Yield	Reaction Conditions	Operation in experiment
77%	With trichlorophosphate Reflux;	4.3. Preparation of 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles (4a-g) and (5a-e) General procedure: A mixture of 4-amino-5-(pyridin-3-yl)-4H-[1,2,4]triazole-3-thiol 3 (1 mmol) and substituted aromatic acids (1.1 mmol) inPOCl3 (5 mL) was refluxed for 6-7 h. The reaction mixture was slowly poured into crushed ice with stirring and neutralized with sodium bicarbonate. Solid material was filtered, washed with cold water, dried, and recrystallized from ethanol to afford 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles 4a-g and 5a-e [25].

Reference： [1]Khan, Imtiaz; Zaib, Sumera; Ibrar, Aliya; Rama, Nasim Hasan; Simpson, Jim; Iqbal, Jamshed [European Journal of Medicinal Chemistry, 2014, vol. 78, p. 167 - 177]

53
[ 36209-51-5 ]
[ 6324-11-4 ]
[ 1607018-33-6 ]

Yield	Reaction Conditions	Operation in experiment
76%	With trichlorophosphate Reflux;	4.3. Preparation of 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles (4a-g) and (5a-e) General procedure: A mixture of 4-amino-5-(pyridin-3-yl)-4H-[1,2,4]triazole-3-thiol 3 (1 mmol) and substituted aromatic acids (1.1 mmol) inPOCl3 (5 mL) was refluxed for 6-7 h. The reaction mixture was slowly poured into crushed ice with stirring and neutralized with sodium bicarbonate. Solid material was filtered, washed with cold water, dried, and recrystallized from ethanol to afford 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles 4a-g and 5a-e [25].

Reference： [1]Khan, Imtiaz; Zaib, Sumera; Ibrar, Aliya; Rama, Nasim Hasan; Simpson, Jim; Iqbal, Jamshed [European Journal of Medicinal Chemistry, 2014, vol. 78, p. 167 - 177]

54
[ 36209-51-5 ]
[ 1878-84-8 ]
[ 1607018-34-7 ]

Yield	Reaction Conditions	Operation in experiment
72%	With trichlorophosphate Reflux;	4.3. Preparation of 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles (4a-g) and (5a-e) General procedure: A mixture of 4-amino-5-(pyridin-3-yl)-4H-[1,2,4]triazole-3-thiol 3 (1 mmol) and substituted aromatic acids (1.1 mmol) inPOCl3 (5 mL) was refluxed for 6-7 h. The reaction mixture was slowly poured into crushed ice with stirring and neutralized with sodium bicarbonate. Solid material was filtered, washed with cold water, dried, and recrystallized from ethanol to afford 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles 4a-g and 5a-e [25].

Reference： [1]Khan, Imtiaz; Zaib, Sumera; Ibrar, Aliya; Rama, Nasim Hasan; Simpson, Jim; Iqbal, Jamshed [European Journal of Medicinal Chemistry, 2014, vol. 78, p. 167 - 177]

55
[ 36209-51-5 ]
[ 1877-75-4 ]
[ 1438398-32-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	With dmap; tetrabutylammomium bromide; trichlorophosphate Microwave irradiation; Heating;
76%	With trichlorophosphate Reflux;	4.3. Preparation of 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles (4a-g) and (5a-e) General procedure: A mixture of 4-amino-5-(pyridin-3-yl)-4H-[1,2,4]triazole-3-thiol 3 (1 mmol) and substituted aromatic acids (1.1 mmol) inPOCl3 (5 mL) was refluxed for 6-7 h. The reaction mixture was slowly poured into crushed ice with stirring and neutralized with sodium bicarbonate. Solid material was filtered, washed with cold water, dried, and recrystallized from ethanol to afford 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles 4a-g and 5a-e [25].

Reference： [1]Li, Ziqiang; Liu, Yishuang; Bai, Xiaoguang; Deng, Qi; Wang, Juxian; Zhang, Guoning; Xiao, Chunling; Mei, Yaning; Wang, Yucheng [RSC Advances, 2015, vol. 5, # 118, p. 97089 - 97101]
[2]Khan, Imtiaz; Zaib, Sumera; Ibrar, Aliya; Rama, Nasim Hasan; Simpson, Jim; Iqbal, Jamshed [European Journal of Medicinal Chemistry, 2014, vol. 78, p. 167 - 177]

56
[ 36209-51-5 ]
[ 405-79-8 ]
[ 791824-11-8 ]

Yield	Reaction Conditions	Operation in experiment
79%	With trichlorophosphate;Reflux;	General procedure: A mixture of 4-amino-5-(pyridin-3-yl)-4H-[1,2,4]triazole-3-thiol 3 (1 mmol) and substituted aromatic acids (1.1 mmol) inPOCl3 (5 mL) was refluxed for 6-7 h. The reaction mixture was slowly poured into crushed ice with stirring and neutralized with sodium bicarbonate. Solid material was filtered, washed with cold water, dried, and recrystallized from ethanol to afford 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles 4a-g and 5a-e [25].

Reference： [1]RSC Advances,2015,vol. 5,p. 97089 - 97101
[2]European Journal of Medicinal Chemistry,2014,vol. 78,p. 167 - 177

57
[ 36209-51-5 ]
[ 5000-65-7 ]
[ 1003514-37-1 ]

Yield	Reaction Conditions	Operation in experiment
72%	In ethanol Reflux;	4.4. Preparation of 1,2,4-triazolo[3,4-b][1,3,4]-thiadiazines (6aeh) General procedure: A mixture of 4-amino-5-(pyridin-4-yl)-4H-[1,2,4]triazole-3-thiol 5 (1 mmol) and substituted phenacyl bromides (1.2 mmol) was refluxed in absolute ethanol (10 mL) for 6-7 h. The reactionmass was poured into crushed ice and neutralized with sodium bicarbonate. Solid product obtained was filtered, washed with water, dried and recrystallized from ethanol to afford conjugated products 6a-h [28].

Reference： [1]Khan, Imtiaz; Zaib, Sumera; Ibrar, Aliya; Rama, Nasim Hasan; Simpson, Jim; Iqbal, Jamshed [European Journal of Medicinal Chemistry, 2014, vol. 78, p. 167 - 177]

58
[ 36209-51-5 ]
[ 41011-01-2 ]
[ 1607018-35-8 ]

Yield	Reaction Conditions	Operation in experiment
75%	In ethanol Reflux;	4.4. Preparation of 1,2,4-triazolo[3,4-b][1,3,4]-thiadiazines (6aeh) General procedure: A mixture of 4-amino-5-(pyridin-4-yl)-4H-[1,2,4]triazole-3-thiol 5 (1 mmol) and substituted phenacyl bromides (1.2 mmol) was refluxed in absolute ethanol (10 mL) for 6-7 h. The reactionmass was poured into crushed ice and neutralized with sodium bicarbonate. Solid product obtained was filtered, washed with water, dried and recrystallized from ethanol to afford conjugated products 6a-h [28].

Reference： [1]Khan, Imtiaz; Zaib, Sumera; Ibrar, Aliya; Rama, Nasim Hasan; Simpson, Jim; Iqbal, Jamshed [European Journal of Medicinal Chemistry, 2014, vol. 78, p. 167 - 177]

59
[ 36209-51-5 ]
[ 53631-18-8 ]
[ 1607018-36-9 ]

Yield	Reaction Conditions	Operation in experiment
78%	In ethanol Reflux;	4.4. Preparation of 1,2,4-triazolo[3,4-b][1,3,4]-thiadiazines (6aeh) General procedure: A mixture of 4-amino-5-(pyridin-4-yl)-4H-[1,2,4]triazole-3-thiol 5 (1 mmol) and substituted phenacyl bromides (1.2 mmol) was refluxed in absolute ethanol (10 mL) for 6-7 h. The reactionmass was poured into crushed ice and neutralized with sodium bicarbonate. Solid product obtained was filtered, washed with water, dried and recrystallized from ethanol to afford conjugated products 6a-h [28].

Reference： [1]Khan, Imtiaz; Zaib, Sumera; Ibrar, Aliya; Rama, Nasim Hasan; Simpson, Jim; Iqbal, Jamshed [European Journal of Medicinal Chemistry, 2014, vol. 78, p. 167 - 177]

60
[ 36209-51-5 ]
[ 135-73-9 ]
[ 517906-11-5 ]

Yield	Reaction Conditions	Operation in experiment
75%	In ethanol Reflux;	4.4. Preparation of 1,2,4-triazolo[3,4-b][1,3,4]-thiadiazines (6aeh) General procedure: A mixture of 4-amino-5-(pyridin-4-yl)-4H-[1,2,4]triazole-3-thiol 5 (1 mmol) and substituted phenacyl bromides (1.2 mmol) was refluxed in absolute ethanol (10 mL) for 6-7 h. The reactionmass was poured into crushed ice and neutralized with sodium bicarbonate. Solid product obtained was filtered, washed with water, dried and recrystallized from ethanol to afford conjugated products 6a-h [28].

Reference： [1]Khan, Imtiaz; Zaib, Sumera; Ibrar, Aliya; Rama, Nasim Hasan; Simpson, Jim; Iqbal, Jamshed [European Journal of Medicinal Chemistry, 2014, vol. 78, p. 167 - 177]

61
[ 36209-51-5 ]
[ 13686-51-6 ]
[ 1607018-37-0 ]

Yield	Reaction Conditions	Operation in experiment
71%	In ethanol Reflux;	4.4. Preparation of 1,2,4-triazolo[3,4-b][1,3,4]-thiadiazines (6aeh) General procedure: A mixture of 4-amino-5-(pyridin-4-yl)-4H-[1,2,4]triazole-3-thiol 5 (1 mmol) and substituted phenacyl bromides (1.2 mmol) was refluxed in absolute ethanol (10 mL) for 6-7 h. The reactionmass was poured into crushed ice and neutralized with sodium bicarbonate. Solid product obtained was filtered, washed with water, dried and recrystallized from ethanol to afford conjugated products 6a-h [28].

Reference： [1]Khan, Imtiaz; Zaib, Sumera; Ibrar, Aliya; Rama, Nasim Hasan; Simpson, Jim; Iqbal, Jamshed [European Journal of Medicinal Chemistry, 2014, vol. 78, p. 167 - 177]

62
[ 36209-51-5 ]
[ 2227-64-7 ]
[ 380651-25-2 ]

Yield	Reaction Conditions	Operation in experiment
73%	In ethanol Reflux;	4.4. Preparation of 1,2,4-triazolo[3,4-b][1,3,4]-thiadiazines (6aeh) General procedure: A mixture of 4-amino-5-(pyridin-4-yl)-4H-[1,2,4]triazole-3-thiol 5 (1 mmol) and substituted phenacyl bromides (1.2 mmol) was refluxed in absolute ethanol (10 mL) for 6-7 h. The reactionmass was poured into crushed ice and neutralized with sodium bicarbonate. Solid product obtained was filtered, washed with water, dried and recrystallized from ethanol to afford conjugated products 6a-h [28].

Reference： [1]Khan, Imtiaz; Zaib, Sumera; Ibrar, Aliya; Rama, Nasim Hasan; Simpson, Jim; Iqbal, Jamshed [European Journal of Medicinal Chemistry, 2014, vol. 78, p. 167 - 177]

63
[ 36209-51-5 ]
[ 2632-10-2 ]
[ 849910-62-9 ]

Yield	Reaction Conditions	Operation in experiment
79%	In ethanol;Reflux;	General procedure: A mixture of 4-amino-5-(pyridin-4-yl)-4H-[1,2,4]triazole-3-thiol 5 (1 mmol) and substituted phenacyl bromides (1.2 mmol) was refluxed in absolute ethanol (10 mL) for 6-7 h. The reactionmass was poured into crushed ice and neutralized with sodium bicarbonate. Solid product obtained was filtered, washed with water, dried and recrystallized from ethanol to afford conjugated products 6a-h [28].

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 78,p. 167 - 177

64
[ 36209-51-5 ]
[ 75-36-5 ]
N-(3-mercapto-5-(pyridin-4-yl)-4H-1,2,4-triazol-4-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With triethylamine In N,N-dimethyl-formamide for 5h; Reflux;	4.1.2. General method for the preparation of compounds 3a,b General procedure: A mixture of 4-amino-5-pyridin-4-yl-4H-[1,2,4]triazole-3-thiol(2) (0.01 mol) and the appropriate acid chloride (0.01 mol) was heated under reflux in DMF in presence of triethylamine (0.5 mL) for 5 h. The reaction mixture was allowed to cool, poured onto ice cold water and acidified by HCl. The obtained white solid wasfiltered, washed with water, dried and crystallized from ethanol.

Reference： [1]Kamel, Mona M.; Megally Abdo, Nadia Y. [European Journal of Medicinal Chemistry, 2014, vol. 86, p. 75 - 80]

65
[ 36209-51-5 ]
[ 122-04-3 ]
N-(3-mercapto-5-(pyridin-4-yl)-4H-1,2,4-triazol-4-yl)-4-nitrobenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With triethylamine In N,N-dimethyl-formamide for 5h; Reflux;	4.1.2. General method for the preparation of compounds 3a,b General procedure: A mixture of 4-amino-5-pyridin-4-yl-4H-[1,2,4]triazole-3-thiol(2) (0.01 mol) and the appropriate acid chloride (0.01 mol) was heated under reflux in DMF in presence of triethylamine (0.5 mL) for 5 h. The reaction mixture was allowed to cool, poured onto ice cold water and acidified by HCl. The obtained white solid wasfiltered, washed with water, dried and crystallized from ethanol.

Reference： [1]Kamel, Mona M.; Megally Abdo, Nadia Y. [European Journal of Medicinal Chemistry, 2014, vol. 86, p. 75 - 80]

66
[ 36209-51-5 ]
[ 2131-55-7 ]
1-(4-chlorophenyl)-3-(3-mercapto-5-(pyridin-4-yl)-4H-1,2,4-triazol-4-yl)thiourea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With pyridine for 0.5h; Reflux;	4.1.6. General method for the preparation of compounds 7a-d General procedure: An equimolar mixture (0.01 mol) of 4-amino-5-pyridin-4-yl-4H-[1,2,4]triazole-3-thiol (2) and the appropriate aryl isothiocyanate was heated under reflux in pyridine (10 mL) for 30 min. The reaction mixture was poured onto ice cold water. The obtained solid was filtered, washed with water, dried and crystallized from ethanol.

Reference： [1]Kamel, Mona M.; Megally Abdo, Nadia Y. [European Journal of Medicinal Chemistry, 2014, vol. 86, p. 75 - 80]

67
[ 36209-51-5 ]
[ 2131-55-7 ]
N-(4-chlorophenyl)-3-(pyridin-4-yl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With pyridine Reflux;	4.1.6. General method for the preparation of compounds 8a-d General procedure: An equimolar mixture (0.01 mol) of 4-amino-5-pyridin-4-yl-4H-[1,2,4]triazole-3-thiol (2) and the appropriate aryl isothiocyanate was heated under reflux in pyridine (10 mL) for 2-3 h until the complete evolution of H2S (detected by lead acetate paper). The reaction mixture was poured onto ice cold water. The obtained solid was filtered, washed with water, dried and crystallized from ethanol.

Reference： [1]Kamel, Mona M.; Megally Abdo, Nadia Y. [European Journal of Medicinal Chemistry, 2014, vol. 86, p. 75 - 80]

68
[ 36209-51-5 ]
[ 2284-20-0 ]
1-(3-mercapto-5-(pyridin-4-yl)-4H-1,2,4-triazol-4-yl)-3-(4-methoxyphenyl)thiourea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With pyridine for 0.5h; Reflux;	4.1.6. General method for the preparation of compounds 7a-d General procedure: An equimolar mixture (0.01 mol) of 4-amino-5-pyridin-4-yl-4H-[1,2,4]triazole-3-thiol (2) and the appropriate aryl isothiocyanate was heated under reflux in pyridine (10 mL) for 30 min. The reaction mixture was poured onto ice cold water. The obtained solid was filtered, washed with water, dried and crystallized from ethanol.

Reference： [1]Kamel, Mona M.; Megally Abdo, Nadia Y. [European Journal of Medicinal Chemistry, 2014, vol. 86, p. 75 - 80]

69
[ 36209-51-5 ]
[ 2284-20-0 ]
N-(4-methoxyphenyl)-3-(pyridin-4-yl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With pyridine Reflux;	4.1.6. General method for the preparation of compounds 8a-d General procedure: An equimolar mixture (0.01 mol) of 4-amino-5-pyridin-4-yl-4H-[1,2,4]triazole-3-thiol (2) and the appropriate aryl isothiocyanate was heated under reflux in pyridine (10 mL) for 2-3 h until the complete evolution of H2S (detected by lead acetate paper). The reaction mixture was poured onto ice cold water. The obtained solid was filtered, washed with water, dried and crystallized from ethanol.

Reference： [1]Kamel, Mona M.; Megally Abdo, Nadia Y. [European Journal of Medicinal Chemistry, 2014, vol. 86, p. 75 - 80]

70
[ 36209-51-5 ]
[ 622-59-3 ]
1-(3-mercapto-5-(pyridin-4-yl)-4H-1,2,4-triazol-4-yl)-3-(p-tolyl)thiourea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With pyridine for 0.5h; Reflux;	4.1.6. General method for the preparation of compounds 7a-d General procedure: An equimolar mixture (0.01 mol) of 4-amino-5-pyridin-4-yl-4H-[1,2,4]triazole-3-thiol (2) and the appropriate aryl isothiocyanate was heated under reflux in pyridine (10 mL) for 30 min. The reaction mixture was poured onto ice cold water. The obtained solid was filtered, washed with water, dried and crystallized from ethanol.

Reference： [1]Kamel, Mona M.; Megally Abdo, Nadia Y. [European Journal of Medicinal Chemistry, 2014, vol. 86, p. 75 - 80]

71
[ 36209-51-5 ]
[ 622-59-3 ]
N-(4-methylphenyl)-3-(pyridin-4-yl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With pyridine Reflux;	4.1.6. General method for the preparation of compounds 8a-d General procedure: An equimolar mixture (0.01 mol) of 4-amino-5-pyridin-4-yl-4H-[1,2,4]triazole-3-thiol (2) and the appropriate aryl isothiocyanate was heated under reflux in pyridine (10 mL) for 2-3 h until the complete evolution of H2S (detected by lead acetate paper). The reaction mixture was poured onto ice cold water. The obtained solid was filtered, washed with water, dried and crystallized from ethanol.

Reference： [1]Kamel, Mona M.; Megally Abdo, Nadia Y. [European Journal of Medicinal Chemistry, 2014, vol. 86, p. 75 - 80]

72
[ 36209-51-5 ]
[ 1985-12-2 ]
1-(4-bromophenyl)-3-(3-mercapto-5-(pyridin-4-yl)-4H-1,2,4-triazol-4-yl)thiourea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With pyridine for 0.5h; Reflux;	4.1.6. General method for the preparation of compounds 7a-d General procedure: An equimolar mixture (0.01 mol) of 4-amino-5-pyridin-4-yl-4H-[1,2,4]triazole-3-thiol (2) and the appropriate aryl isothiocyanate was heated under reflux in pyridine (10 mL) for 30 min. The reaction mixture was poured onto ice cold water. The obtained solid was filtered, washed with water, dried and crystallized from ethanol.

Reference： [1]Kamel, Mona M.; Megally Abdo, Nadia Y. [European Journal of Medicinal Chemistry, 2014, vol. 86, p. 75 - 80]

73
[ 36209-51-5 ]
[ 1985-12-2 ]
N-(p-bromophenyl)-3-(pyridin-4-yl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With pyridine Reflux;	4.1.6. General method for the preparation of compounds 8a-d General procedure: An equimolar mixture (0.01 mol) of 4-amino-5-pyridin-4-yl-4H-[1,2,4]triazole-3-thiol (2) and the appropriate aryl isothiocyanate was heated under reflux in pyridine (10 mL) for 2-3 h until the complete evolution of H2S (detected by lead acetate paper). The reaction mixture was poured onto ice cold water. The obtained solid was filtered, washed with water, dried and crystallized from ethanol.

Reference： [1]Kamel, Mona M.; Megally Abdo, Nadia Y. [European Journal of Medicinal Chemistry, 2014, vol. 86, p. 75 - 80]

74
[ 36209-51-5 ]
mercury(II) iodide [ No CAS ]
[Hg(4-aptt)₂] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	In ethanol; water; N,N-dimethyl-formamide at 20℃;	Preparation of [Hg(4-aptt)2] (2) A mixture of 4-Haptt (0.0116 g, 0.06 mmol), HgI2 (0.0136 g,0.03 mmol), DMF (1 mL), and water/ethanol (7 mL, 3:4) was stirred at room temperature. The dark yellow solution was kept undisturbed for two weeks and slight yellow block crystals were isolated from the solution. Yield: 66%. Anal.Calcd. for C14H12HgN10S2 (%): C, 28.74; H, 2.05; N, 23.95. Found: C, 28.55; H, 2.16; N, 24.13. IR (solid KBr pellets, cm-1): 3287 (m), 3182 (w), 1604 (s), 1515 (w), 1455 (m),1297 (w), 1278 (w), 1047 (w), 992 (m), 833 (m), 708 (m), 662 (m).

Reference： [1]Si, Xiaoqin; Li, Linke; Fan, Liyan; Wang, Changhong; Qiao, Min; Hou, Hongwei [Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 2015, vol. 45, # 6, p. 906 - 913]

75
[ 98-03-3 ]
[ 36209-51-5 ]
(E)-5-(pyridin-4-yl)-4-((thiophen-2-ylmethylene)amino)-4H-1,2,4-triazole-3-thiol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	In acetic acid at 20℃; for 10h; Reflux;	General procedure for the synthesis of ligands L1-L2 General procedure: Intermediate triazoles 3a was synthesized from corresponding acid hydrazide (1a) through multi-step reactions (Scheme 1) as per the reported literature [13-14]. The hydrazide was converted to potassium salt (2a) by reacting with carbon disulfide and potassium hydroxide in absolute ethanol. On reacting with hydrazine hydrate, the salt undergoes ring closure to yield the triazole, 3a. The desired Schiff base L1 was obtained in good yield by refluxing equimolar amount of 4-amino-5-(pyridin-4-yl)-4H-1,2,4-triazole-3-thiol (3a) with thiophene-2-carbaldehyde using acetic acid as a solvent. The mixture was stirred at room temperature for 10 h (Scheme 1). The reaction mixture was kept overnight, pale yellow product was precipitated out. It was filtered, washed with ice cold water, methanol and recrystallized with a mixture of DMF & methanol. The same procedure was used for the synthesis of ligand L2.

Reference： [1]Tyagi, Prateek; Chandra, Sulekh; Saraswat; Yadav, Deepak [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2015, vol. 145, p. 155 - 164]

76
[ 98-01-1 ]
[ 36209-51-5 ]
(E)-4-((furan-2-ylmethylene)amino)-5-(pyridin-4-yl)-4H-1,2,4-triazole-3-thiol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	In acetic acid at 20℃; for 10h; Reflux;	General procedure for the synthesis of ligands L1-L2 General procedure: Intermediate triazoles 3a was synthesized from corresponding acid hydrazide (1a) through multi-step reactions (Scheme 1) as per the reported literature [13-14]. The hydrazide was converted to potassium salt (2a) by reacting with carbon disulfide and potassium hydroxide in absolute ethanol. On reacting with hydrazine hydrate, the salt undergoes ring closure to yield the triazole, 3a. The desired Schiff base L1 was obtained in good yield by refluxing equimolar amount of 4-amino-5-(pyridin-4-yl)-4H-1,2,4-triazole-3-thiol (3a) with thiophene-2-carbaldehyde using acetic acid as a solvent. The mixture was stirred at room temperature for 10 h (Scheme 1). The reaction mixture was kept overnight, pale yellow product was precipitated out. It was filtered, washed with ice cold water, methanol and recrystallized with a mixture of DMF & methanol. The same procedure was used for the synthesis of ligand L2.

Reference： [1]Tyagi, Prateek; Chandra, Sulekh; Saraswat; Yadav, Deepak [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2015, vol. 145, p. 155 - 164]

77
[ 36209-51-5 ]
[ 100-52-7 ]
4-(benzylideneamino)-3-mercapto-5-pyridin-4-yl-4H-1,2,4-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85.41%	In N,N-dimethyl-formamide for 0.0166667h; Microwave irradiation;	Method B - Microwave General procedure: 4-Amino-3-mercapto-5-pyridin-4-yl-4H-1,2,4-triazole (0.965 g, 0.005 mol) was taken in a RB flask, dissolved in minimum amount of DMF (5 mL) and then required amount of respective aryl aldehyde (0.005 mol) added to this solution. The RB flask was kept in a beaker and microwave irradiation was carried out for 1-1.5 min at 900 W until the solution become yellowish in colour. The resulting solution was poured onto crushed ice. The precipitate which got separated was dried and purified by recrystallization from methanol. The homogeneity of the product was checked by melting point and TLC using ethyl acetate methanol (1:1) as developing solvent and iodine vapor as visualizing agent.
	With hydrogenchloride In methanol; water for 3h; Reflux;	2.1.3. Synthesis of 4-[(substituted phenyl)-methylene]-amino-5-(pyridine-4-yl)-4H-1,2,4-triazol-3-thiol (4a-4g) [17] General procedure: To a suspension of corresponding compound 1,2,4-triazole-3-thiol (3) (0.005 mol) in methanol (50 ml) and an equimolar quantity of aromatic aldehyde in methanol (20 ml) was mixed. This suspension was heated until a clear solution was obtained and refluxed for 3h in the presence of a few drops of concentrated hydrochloric acid in a water bath. The reaction solution was left undisturbed overnight. On the next day, the separated solid was filtered, washed with ethanol and recrystallized from ethanol to procure the product/ compound (4).

Reference： [1]Majumder, Sujan; Bashyal, Bishnu Maya; Gupta [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 10, p. 1260 - 1274]
[2]Rajoriya, Vaibhav; Kashaw, Varsha; Kashaw, Sushil K. [Letters in drug design and discovery, 2018, vol. 15, # 5, p. 451 - 462]

78
[ 36209-51-5 ]
[ 529-20-4 ]
4-(2-methylbenzylideneamino)-3-mercapto-5-pyridin-4-yl-4H-1,2,4-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81.36%	In N,N-dimethyl-formamide for 0.0166667h; Microwave irradiation;	Method B - Microwave General procedure: 4-Amino-3-mercapto-5-pyridin-4-yl-4H-1,2,4-triazole (0.965 g, 0.005 mol) was taken in a RB flask, dissolved in minimum amount of DMF (5 mL) and then required amount of respective aryl aldehyde (0.005 mol) added to this solution. The RB flask was kept in a beaker and microwave irradiation was carried out for 1-1.5 min at 900 W until the solution become yellowish in colour. The resulting solution was poured onto crushed ice. The precipitate which got separated was dried and purified by recrystallization from methanol. The homogeneity of the product was checked by melting point and TLC using ethyl acetate methanol (1:1) as developing solvent and iodine vapor as visualizing agent.

Reference： [1]Majumder, Sujan; Bashyal, Bishnu Maya; Gupta [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 10, p. 1260 - 1274]

79
[ 36209-51-5 ]
[ 620-23-5 ]
4-(3-methylbenzylideneamino)-3-mercapto-5-pyridin-4-yl-4H-1,2,4-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94.92%	In N,N-dimethyl-formamide for 0.0166667h; Microwave irradiation;	Method B - Microwave General procedure: 4-Amino-3-mercapto-5-pyridin-4-yl-4H-1,2,4-triazole (0.965 g, 0.005 mol) was taken in a RB flask, dissolved in minimum amount of DMF (5 mL) and then required amount of respective aryl aldehyde (0.005 mol) added to this solution. The RB flask was kept in a beaker and microwave irradiation was carried out for 1-1.5 min at 900 W until the solution become yellowish in colour. The resulting solution was poured onto crushed ice. The precipitate which got separated was dried and purified by recrystallization from methanol. The homogeneity of the product was checked by melting point and TLC using ethyl acetate methanol (1:1) as developing solvent and iodine vapor as visualizing agent.

Reference： [1]Majumder, Sujan; Bashyal, Bishnu Maya; Gupta [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 10, p. 1260 - 1274]

80
[ 36209-51-5 ]
[ 135-02-4 ]
4-(2-methoxybenzylideneamino)-3-mercapto-5-pyridin-4-yl-4H-1,2,4-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90.03%	In N,N-dimethyl-formamide for 0.0166667h; Microwave irradiation;	Method B - Microwave General procedure: 4-Amino-3-mercapto-5-pyridin-4-yl-4H-1,2,4-triazole (0.965 g, 0.005 mol) was taken in a RB flask, dissolved in minimum amount of DMF (5 mL) and then required amount of respective aryl aldehyde (0.005 mol) added to this solution. The RB flask was kept in a beaker and microwave irradiation was carried out for 1-1.5 min at 900 W until the solution become yellowish in colour. The resulting solution was poured onto crushed ice. The precipitate which got separated was dried and purified by recrystallization from methanol. The homogeneity of the product was checked by melting point and TLC using ethyl acetate methanol (1:1) as developing solvent and iodine vapor as visualizing agent.

Reference： [1]Majumder, Sujan; Bashyal, Bishnu Maya; Gupta [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 10, p. 1260 - 1274]

81
[ 36209-51-5 ]
[ 591-31-1 ]
4-(3-methoxybenzylideneamino)-3-mercapto-5-pyridin-4-yl-4H-1,2,4-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83.6%	In N,N-dimethyl-formamide for 0.0166667h; Microwave irradiation;	Method B - Microwave General procedure: 4-Amino-3-mercapto-5-pyridin-4-yl-4H-1,2,4-triazole (0.965 g, 0.005 mol) was taken in a RB flask, dissolved in minimum amount of DMF (5 mL) and then required amount of respective aryl aldehyde (0.005 mol) added to this solution. The RB flask was kept in a beaker and microwave irradiation was carried out for 1-1.5 min at 900 W until the solution become yellowish in colour. The resulting solution was poured onto crushed ice. The precipitate which got separated was dried and purified by recrystallization from methanol. The homogeneity of the product was checked by melting point and TLC using ethyl acetate methanol (1:1) as developing solvent and iodine vapor as visualizing agent.

Reference： [1]Majumder, Sujan; Bashyal, Bishnu Maya; Gupta [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 10, p. 1260 - 1274]

82
[ 36209-51-5 ]
[ 123-08-0 ]
4-(4-hydroxybenzylideneamino)-3-mercapto-5-pyridin-4-yl-4H-1,2,4-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87.54%	In N,N-dimethyl-formamide for 0.025h; Microwave irradiation;	Method B - Microwave General procedure: 4-Amino-3-mercapto-5-pyridin-4-yl-4H-1,2,4-triazole (0.965 g, 0.005 mol) was taken in a RB flask, dissolved in minimum amount of DMF (5 mL) and then required amount of respective aryl aldehyde (0.005 mol) added to this solution. The RB flask was kept in a beaker and microwave irradiation was carried out for 1-1.5 min at 900 W until the solution become yellowish in colour. The resulting solution was poured onto crushed ice. The precipitate which got separated was dried and purified by recrystallization from methanol. The homogeneity of the product was checked by melting point and TLC using ethyl acetate methanol (1:1) as developing solvent and iodine vapor as visualizing agent.
65%	In methanol Reflux;	Synthesis of 4-(4-substituted benzylideneamino)-5-(pyridine-4-yl)-4H-1,2,4-triazole-3-thiol (4a-f) : General procedure General procedure: Equimolar quantities of compound (3) (0.001 mol)and p-substituted benzaldehydes (0.001 mol) were dissolved in methanol. The mixture was refluxed on water bath for about 10-14 hr. Progress of the reaction was monitored by TLC. The solution was poured inice cold water and the resulting solid was filtered,washed and recrystallized with suitable solvents viz.methanol, ethanol, acetone and benzene theirphysicochemical data mentioned are in Table-1.

Reference： [1]Majumder, Sujan; Bashyal, Bishnu Maya; Gupta [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 10, p. 1260 - 1274]
[2]Sabale, Prafulla M.; Mehta, Pooja [Indian Journal of Heterocyclic Chemistry, 2013, vol. 23, # 2, p. 149 - 154]

83
[ 36209-51-5 ]
[ 6630-33-7 ]
4-(2-bromobenzylideneamino)-3-mercapto-5-pyridin-4-yl-4H-1,2,4-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72.22%	In N,N-dimethyl-formamide for 0.0166667h; Microwave irradiation;	Method B - Microwave General procedure: 4-Amino-3-mercapto-5-pyridin-4-yl-4H-1,2,4-triazole (0.965 g, 0.005 mol) was taken in a RB flask, dissolved in minimum amount of DMF (5 mL) and then required amount of respective aryl aldehyde (0.005 mol) added to this solution. The RB flask was kept in a beaker and microwave irradiation was carried out for 1-1.5 min at 900 W until the solution become yellowish in colour. The resulting solution was poured onto crushed ice. The precipitate which got separated was dried and purified by recrystallization from methanol. The homogeneity of the product was checked by melting point and TLC using ethyl acetate methanol (1:1) as developing solvent and iodine vapor as visualizing agent.

Reference： [1]Majumder, Sujan; Bashyal, Bishnu Maya; Gupta [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 10, p. 1260 - 1274]

84
[ 36209-51-5 ]
[ 1122-91-4 ]
4-(4-bromobenzylideneamino)-3-mercapto-5-pyridin-4-yl-4H-1,2,4-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83.33%	In N,N-dimethyl-formamide for 0.0166667h; Microwave irradiation;	Method B - Microwave General procedure: 4-Amino-3-mercapto-5-pyridin-4-yl-4H-1,2,4-triazole (0.965 g, 0.005 mol) was taken in a RB flask, dissolved in minimum amount of DMF (5 mL) and then required amount of respective aryl aldehyde (0.005 mol) added to this solution. The RB flask was kept in a beaker and microwave irradiation was carried out for 1-1.5 min at 900 W until the solution become yellowish in colour. The resulting solution was poured onto crushed ice. The precipitate which got separated was dried and purified by recrystallization from methanol. The homogeneity of the product was checked by melting point and TLC using ethyl acetate methanol (1:1) as developing solvent and iodine vapor as visualizing agent.
69%	In methanol Reflux;	Synthesis of 4-(4-substituted benzylideneamino)-5-(pyridine-4-yl)-4H-1,2,4-triazole-3-thiol (4a-f) : General procedure General procedure: Equimolar quantities of compound (3) (0.001 mol)and p-substituted benzaldehydes (0.001 mol) were dissolved in methanol. The mixture was refluxed on water bath for about 10-14 hr. Progress of the reaction was monitored by TLC. The solution was poured inice cold water and the resulting solid was filtered,washed and recrystallized with suitable solvents viz.methanol, ethanol, acetone and benzene theirphysicochemical data mentioned are in Table-1.

Reference： [1]Majumder, Sujan; Bashyal, Bishnu Maya; Gupta [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 10, p. 1260 - 1274]
[2]Sabale, Prafulla M.; Mehta, Pooja [Indian Journal of Heterocyclic Chemistry, 2013, vol. 23, # 2, p. 149 - 154]

85
[ 36209-51-5 ]
[ 446-52-6 ]
4-(2-fluorobenzylideneamino)-3-mercapto-5-pyridin-4-yl-4H-1,2,4-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86.96%	In N,N-dimethyl-formamide for 0.025h; Microwave irradiation;	Method B - Microwave General procedure: 4-Amino-3-mercapto-5-pyridin-4-yl-4H-1,2,4-triazole (0.965 g, 0.005 mol) was taken in a RB flask, dissolved in minimum amount of DMF (5 mL) and then required amount of respective aryl aldehyde (0.005 mol) added to this solution. The RB flask was kept in a beaker and microwave irradiation was carried out for 1-1.5 min at 900 W until the solution become yellowish in colour. The resulting solution was poured onto crushed ice. The precipitate which got separated was dried and purified by recrystallization from methanol. The homogeneity of the product was checked by melting point and TLC using ethyl acetate methanol (1:1) as developing solvent and iodine vapor as visualizing agent.

Reference： [1]Majumder, Sujan; Bashyal, Bishnu Maya; Gupta [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 10, p. 1260 - 1274]

86
[ 36209-51-5 ]
[ 459-57-4 ]
4-(4-fluorobenzylideneamino)-3-mercapto-5-pyridin-4-yl-4H-1,2,4-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93.65%	In N,N-dimethyl-formamide for 0.0166667h; Microwave irradiation;	Method B - Microwave General procedure: 4-Amino-3-mercapto-5-pyridin-4-yl-4H-1,2,4-triazole (0.965 g, 0.005 mol) was taken in a RB flask, dissolved in minimum amount of DMF (5 mL) and then required amount of respective aryl aldehyde (0.005 mol) added to this solution. The RB flask was kept in a beaker and microwave irradiation was carried out for 1-1.5 min at 900 W until the solution become yellowish in colour. The resulting solution was poured onto crushed ice. The precipitate which got separated was dried and purified by recrystallization from methanol. The homogeneity of the product was checked by melting point and TLC using ethyl acetate methanol (1:1) as developing solvent and iodine vapor as visualizing agent.
71%	In methanol Reflux;	Synthesis of 4-(4-substituted benzylideneamino)-5-(pyridine-4-yl)-4H-1,2,4-triazole-3-thiol (4a-f) : General procedure General procedure: Equimolar quantities of compound (3) (0.001 mol)and p-substituted benzaldehydes (0.001 mol) were dissolved in methanol. The mixture was refluxed on water bath for about 10-14 hr. Progress of the reaction was monitored by TLC. The solution was poured inice cold water and the resulting solid was filtered,washed and recrystallized with suitable solvents viz.methanol, ethanol, acetone and benzene theirphysicochemical data mentioned are in Table-1. 4-(4-Fluorobenzylideneamino)-5-(pyridine-4-yl)-4H-1,2,4-triazole-3-thiol (4a)IR (KBr, cm-1): 1604 (C=N str), 1007 (C-S str),2710 (SH str), 1153 (C-F str); 1H NMR (d ppm): 7.79-7.86 (d, 2H, C2 and C6 ArH), 7.61-7.63 (d, 2H, C3 andC5-H), 8.23 (s, 1H, N=CH), 8.79-8.80 (d, 2H, pyridine-C2 and C6-H), 7.89-7.90 (d, 2H, pyridine-C3 and C5-H),2.98 (s, 1H, aromatic C-SH); Mass : m/z 299 (M+).

Reference： [1]Majumder, Sujan; Bashyal, Bishnu Maya; Gupta [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 10, p. 1260 - 1274]
[2]Sabale, Prafulla M.; Mehta, Pooja [Indian Journal of Heterocyclic Chemistry, 2013, vol. 23, # 2, p. 149 - 154]

87
[ 36209-51-5 ]
[ 105-07-7 ]
4-(4-cyanobenzylideneamino)-3-mercapto-5-pyridin-4-yl-4H-1,2,4-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84.97%	In N,N-dimethyl-formamide for 0.0166667h; Microwave irradiation;	Method B - Microwave General procedure: 4-Amino-3-mercapto-5-pyridin-4-yl-4H-1,2,4-triazole (0.965 g, 0.005 mol) was taken in a RB flask, dissolved in minimum amount of DMF (5 mL) and then required amount of respective aryl aldehyde (0.005 mol) added to this solution. The RB flask was kept in a beaker and microwave irradiation was carried out for 1-1.5 min at 900 W until the solution become yellowish in colour. The resulting solution was poured onto crushed ice. The precipitate which got separated was dried and purified by recrystallization from methanol. The homogeneity of the product was checked by melting point and TLC using ethyl acetate methanol (1:1) as developing solvent and iodine vapor as visualizing agent.

Reference： [1]Majumder, Sujan; Bashyal, Bishnu Maya; Gupta [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 10, p. 1260 - 1274]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	36209-51-5	MDL No. :	MFCD00274215
Formula :	C₇H₇N₅S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LHSIJUVRXSETDR-UHFFFAOYSA-N
M.W :	193.23	Pubchem ID :	719823
Synonyms :

Num. heavy atoms :	13
Num. arom. heavy atoms :	11
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	50.65
TPSA :	108.42 Å²

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.3 cm/s

Log Po/w (iLOGP) :	1.16
Log Po/w (XLOGP3) :	0.25
Log Po/w (WLOGP) :	0.35
Log Po/w (MLOGP) :	0.68
Log Po/w (SILICOS-IT) :	0.08
Consensus Log Po/w :	0.5

[ CAS No. 36209-51-5 ] {[proInfo.proName]}

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Medicinal Chemistry

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Application In Synthesis of [ 36209-51-5 ]

[ 36209-51-5 ] Synthesis Path-Downstream 1~87

Related Functional Groups of
[ 36209-51-5 ]

Amines

Hydrazines

Related Parent Nucleus of
[ 36209-51-5 ]

Triazoles

Thiophenols

Pyridines

Precautionary Statements-General

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Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Log S (ESOL) :	-1.76
Solubility :	3.39 mg/ml ; 0.0176 mol/l
Class :	Very soluble
Log S (Ali) :	-2.09
Solubility :	1.58 mg/ml ; 0.00818 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.94
Solubility :	2.23 mg/ml ; 0.0116 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.1

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

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P378
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
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P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
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P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 36209-51-5 ] {[proInfo.proName]}

Quality Control of [ 36209-51-5 ]

Related Doc. of [ 36209-51-5 ]

Product Details of [ 36209-51-5 ]

Calculated chemistry of [ 36209-51-5 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 36209-51-5 ]

Application In Synthesis of [ 36209-51-5 ]

[ 36209-51-5 ] Synthesis Path-Downstream 1~87

Related Functional Groups of [ 36209-51-5 ]

Amines

Hydrazines

Related Parent Nucleus of [ 36209-51-5 ]

Triazoles

Thiophenols

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

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[ 36209-51-5 ]

Related Parent Nucleus of
[ 36209-51-5 ]