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Chemical Structure| 5818-06-4
Chemical Structure| 5818-06-4
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Product Details of [ 5818-06-4 ]

CAS No. :5818-06-4 MDL No. :MFCD00014759
Formula : C7H8N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :OACGSLLKFCMXSX-UHFFFAOYSA-N
M.W : 152.15 Pubchem ID :79889
Synonyms :

Calculated chemistry of [ 5818-06-4 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 3.0
Molar Refractivity : 39.36
TPSA : 75.35 Ų

Pharmacokinetics

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) : -7.28 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.86
Log Po/w (XLOGP3) : -0.08
Log Po/w (WLOGP) : 0.0
Log Po/w (MLOGP) : 0.54
Log Po/w (SILICOS-IT) : -0.28
Consensus Log Po/w : 0.21

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.0
Solubility : 15.1 mg/ml ; 0.099 mol/l
Class : Very soluble
Log S (Ali) : -1.05
Solubility : 13.5 mg/ml ; 0.089 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.45
Solubility : 5.44 mg/ml ; 0.0357 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 5818-06-4 ]

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:

Application In Synthesis of [ 5818-06-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 5818-06-4 ]

[ 5818-06-4 ] Synthesis Path-Downstream   1~92

  • 1
  • [ 7781-98-8 ]
  • [ 5818-06-4 ]
YieldReaction ConditionsOperation in experiment
85% With hydrazine hydrate In ethanol; water Reflux; Synthesis of benzohydrazides General procedure: Hydrazides (30-58) were synthesized by one pot conventionalmethod24 Benzoic acid or its derivative (10 mmol) was dissolvedin ethanol (20 mL). Sulfuric acid (3 N, 2 mL) was added and thereaction contents were refluxed for six hours. The reaction wasmonitored with TLC. After the completion of the reaction, the reactionmixture was neutralized by adding solid NaHCO3, and filteredto remove excess of NaHCO3. In the neutralized reaction mixture which contains ethyl ester, hydrazine monohydrate (1.5 mL,3 mmol) was added and refluxed for 3-6 h to complete the reaction.Ethanol and unreacted hydrazine were removed by distillationupto 1/3 volume. The reaction contents were cooled, filteredand recrystallized from methanol to obtain the desired hydrazidecrystals (see Supporting information).
With hydrazine hydrate
With hydrazine hydrate
With hydrazine hydrate In ethanol for 36h; Reflux;
With hydrazine
With hydrazine In ethanol Heating;
With hydrazine hydrate In ethanol Reflux; 2.1.1.2. General procedure for the synthesis of (2/3/4) un/substitutedbenzhydrazides (3a-3g). General procedure: As displayed in Scheme 2, the un/substitutedester derivative (2a-2g, 1.0 mmol), hydrazine hydrate (1.2 mmol)were taken in ethyl alcohol (10 mL) and the reaction mixture washeated to reflux temperature and maintained until the reaction wascompleted (Checked by TLC) [50a]. After achievement of the reaction,the reaction was progressively cooled to room temperature. Slowly,solid precipitated out in the reaction mass, was filtered, washed withcold ethanol, and dried to afford a product (2/3/4) un/substituted-Benz hydrazides with 80-87% yield (3a-3g).
With hydrazine hydrate In ethanol for 5.25h; Reflux; Hydrazides 1a-1l (general procedure). General procedure: A clean and dry 250-mL round-bottom flask was charged with 5 g of the corresponding ethyl ester and 50 mL of ethanol, and 5 g of hydrazine hydrate was added dropwise with stirring at room temperature over a period of 15 min. The mixture was then refluxed for 5 h (TLC) and concentrated, and the solid product was filtered off and recrystallized from methanol.
With H4N2*5H2O In ethanol Reflux;
With hydrazine hydrate In ethanol for 12h; Reflux; 4.1.3. General procedure for synthesis of carbohydrazides (3a-d) General procedure: A mixture of ester 2a-d (10 mmol) and hydrazine monohydrate 80%(200 mmol) in ethanol (20 ml) was stirred vigorously for 12 h at reflux.After this time, the reaction mixture was kept in the freezer for 1 h. Thesolid formed was filtered and washed with cold ethanol. Compounds 3adwere obtained pure in 72-89% yield.
With hydrazine hydrate In ethanol Reflux;

Reference: [1]Mehr-Un-Nisa; Munawar, Munawar A.; Chattha, Fauzia A.; Kousar, Samina; Munir, Jawaria; Ismail, Tayaba; Ashraf, Muhammad; Khan, Misbahul A. [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 17, p. 6014 - 6024]
[2]Struve; Radenhausen [Journal fur praktische Chemie (Leipzig 1954), 1895, vol. <2> 52, p. 234]
[3]Location in patent: scheme or table Ghani, Usman; Ullah, Nisar [Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 11, p. 4042 - 4048]
[4]Xi, Meiyang; Ge, Jun; Wang, Xiaojian; Sun, Chenbin; Liu, Tianqi; Fang, Liang; Xiao, Qiong; Yin, Dali [Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 14, p. 3218 - 3230]
[5]Oguri, Takahiro; Kawahara, Akie; Kihara, Nobuhiro [Polymer, 2016, vol. 99, p. 83 - 89]
[6]Kaproń, Barbara; Łuszczki, Jarogniew J.; Siwek, Agata; Karcz, Tadeusz; Nowak, Gabriel; Zagaja, Mirosław; Andres-Mach, Marta; Stasiłowicz, Anna; Cielecka-Piontek, Judyta; Kocki, Janusz; Plech, Tomasz [Bioorganic Chemistry, 2020, vol. 94]
[7]Dige, Nilam C.; Hassan, Mubashir; Lee, Ki Hwan; Mahajan, Prasad G.; Raza, Hussain; Seo, Sung-Yum; Vanjare, Balasaheb D. [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2020, vol. 241]
[8]Dhotre, B. K.; Khandebharad, A. U.; Pathan, A.; Raut, S. V. [Russian Journal of Organic Chemistry, 2020, vol. 56, # 7, p. 1324 - 1326]
[9]Babu, Bathini Nagendra; Devi, Ganthala Parimala; Kamal, Ahmed; Kumar, C. Ganesh; Rani Routhu, Sunitha; Shareef, Mohd Adil [RSC Medicinal Chemistry, 2020, vol. 11, # 10, p. 1178 - 1184]
[10]Yamazaki, Diego A.S.; Rozada, Andrew M.F.; Baréa, Paula; Reis, Elaine C.; Basso, Ernani A.; Sarragiotto, Maria Helena; Seixas, Flávio A.V.; Gauze, Gisele F. [Bioorganic and Medicinal Chemistry, 2021, vol. 32]
[11]Kant, Rajni; Yang, Ming-Hui; Tseng, Chih-Hua; Yen, Chia-Hung; Li, Wei-You; Tyan, Yu-Chang; Chen, Marcelo; Tzeng, Cherng-Chyi; Chen, Wei-Cheng; You, Kaiting; Wang, Wen-Chieh; Chen, Yeh-Long; Chen, Yi-Ming Arthur [Journal of Medicinal Chemistry, 2021, vol. 64, # 13, p. 8992 - 9009]
  • 2
  • [ 495-69-2 ]
  • [ 5818-06-4 ]
  • <i>N</i>-hippuroyl-<i>N'</i>-(3-hydroxy-benzoyl)-hydrazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With L-Cysteine; papain
  • 3
  • [ 122-51-0 ]
  • [ 5818-06-4 ]
  • [ 5378-29-0 ]
YieldReaction ConditionsOperation in experiment
86% for 22h; Heating;
In xylene for 6.7h; Heating;
  • 5
  • [ 19438-10-9 ]
  • [ 5818-06-4 ]
YieldReaction ConditionsOperation in experiment
81% With hydrazine hydrate In ethanol for 0.25h; Reflux; Microwave irradiation;
80% With hydrazine hydrate In ethanol for 10h; Reflux; 1 4.4.5.1. 3-Hydroxybenzohydrazide (8) An 80% solution of hydrazinehydrate (1.52 mL, 25 mmol) was added dropwise to a solution ofmethyl 3-hydroxybenzoate (760 mg, 5 mmol) in ethanol (25 mL).The reaction mixture was refluxed for 10 h until completion, asdetermined by TLC. After evaporating approximately half of thesolvent, water (7 mL) was added and the precipitated productwas filtered and washed with a small amount of ethanol and water.White solid, yield 80.0%. 1H NMR (400 MHz, DMSO-d6) d 9.61 (s,1H), 9.60 (s, 1H), 7.21-7.15 (m, 3H), 6.88-6.81 (m, 1H), 4.41 (s,2H). ESI-MS: calcd for [M+H]+ m/z 153.1, found:153.2.
67% With hydrazine hydrate In methanol for 48h; Reflux; 2. General procedure for the synthesis of benzoic acid hydrazides 4b-c General procedure: The synthesis procedure was adapted from the literature [7]. To a solution of substituted benzoicacid methyl ester (10 mmol) in dry CH3OH (25 mL), H2NNH2 × H2O (98%, 1.0 mL, 20 mmol) wasadded. The reaction mixture was stirred and carried out under gentle reflux for two days. Reactionmixture was concentrated before crystallization to obtain the hydrazides 4b-c.
63% With hydrazine hydrate In ethanol; water for 48h; Reflux; 3 A mixture of methyl 3-hydroxybenzoate (6.85 g, 45.0 mmol), hydrazine hydrate (11.2 mL of 80% aqueous solution) and ethanol (60 mL) was heated under reflux for 48 hours and then cooled to room temperature. Washed with cold water and dried to give the target product 4-hydroxybenzohydrazide 4.34g, yield 63%. The resulting 3-hydroxybenzohydrazide (4.34 g, 28.5 mmol) was then mixed with trimethoxymethane (19.7 mL) and heated to reflux for 24 hours. After cooling and removal of excess trimethoxymethane under reduced pressure, the crude product was isolated and purified by silica gel column chromatography to give 4.24 g of the target product in a yield of 92%
47% With hydrazine hydrate In ethanol for 19h; Reflux; 5.1.1. General procedure for the preparation of benzohydrazides(4-13) General procedure: Various benzohydrazides 5-7 and 9-13 were obtained accordingto known procedures [40,65] except for benzohydrazides 4and 8 which were commercially available. A solution of the methylbenzoate (1 equiv) in ethanol was added dropwise to 65% hydrazinemonohydrate (5 equiv). The reaction mixture was then heatedunder reflux and stirred overnight. The reaction progress was followedup by TLC. Crude product was collected by filtration aftercooling of the reaction medium and finally washed with coldethanol unless specified otherwise. The desired benzohydrazides were used without any further purification.The analysis of spectral data (1H and 13C NMR), the yields, HRMS,Mp and Rf of these precursors are presented in SupplementaryInformation.
With hydrazine hydrate In methanol
With hydrazine In water at 60℃;
With hydrazine hydrate Reflux;
6.9 g With hydrazine hydrate In ethanol Reflux; 1.2 Step-2: Preparation of hydroxy benzohydrazide To a stirred solution of methyl 3-hydroxy benzoate (7 g, 46.05 mmol) in ethanol (150 mL) was added hydrazine hydrate (23 g, 460.5 mmol) at room temperature and the reaction mixture was refluxed for 10-12 hrs. The reaction was monitored by TLC; upon disappearance of the starting material, the reaction mass was cooled to room temperature and the ethanol was distilled out to get the crude product. To this crude product was added acetone (20 mL) at 10-15° C. and this was stirred in n-hexane (100 mL) for 30 min. The white solid that precipitated out was filtered and dried under vacuum at 55° C. to obtain the pure product (Yield: 6.9 g, 85.71% of theoretical). (0317) Yield: 95.71% (0318) HPLC Purity: 98.7% (0319) 1H NMR: Consistent with the structure. (0320) LCMS: m/z=153 (MH+)
With hydrazine hydrate In ethanol for 12h; Reflux;
With hydrazine hydrate Reflux;
With hydrazine hydrate In ethanol
With hydrazine hydrate Reflux; Synthesis of acid hydrazide derivatives (3) from esters (2) General procedure: One millimole of the corresponding ester was added insmall portion to a round bottom flask containing solution ofhydrazine hydrate (10 ml) and followed by stirring themixture under reflux conditions. When completion of thereaction was monitored by TLC, the media was poured ontoice bath and the resulting precipitation was isolated by filtration.The corresponding acid hydrazide was afforded andrecrystallized from ethanol and water.
With hydrazine hydrate In methanol Reflux;

Reference: [1]Zaheer, Muhammad; Zia-Ur-Rehman, Muhammad; Rahman, Salma; Ahmed, Naveed; Chaudhary, Muhammad Nawaz [Journal of the Chilean Chemical Society, 2012, vol. 57, # 4, p. 1492 - 1496]
[2]Gao, Dingding; Li, Yingxia [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 14, p. 3780 - 3791]
[3]Giurg, Mirosław; Maniak, Halina; Matyja, Konrad; Talma, Michał; Trusek, Anna [Molecules, 2020, vol. 25, # 5]
[4]Current Patent Assignee: ZHEJIANG UNIVERSITY OF TECHNOLOGY - CN107266505, 2017, A Location in patent: Paragraph 0048; 0050
[5]Ameryckx, Alice; Thabault, Léopold; Pochet, Lionel; Leimanis, Serge; Poupaert, Jacques H.; Wouters, Johan; Joris, Bernard; Van Bambeke, Françoise; Frédérick, Raphaël [European Journal of Medicinal Chemistry, 2018, vol. 159, p. 324 - 338]
[6]Schlecker; Thieme [Tetrahedron, 1988, vol. 44, # 11, p. 3289 - 3294]
[7]Rando, Daniela G.; Avery, Mitchell A.; Tekwani, Babu L.; Khan, Shabana I.; Ferreira, Elizabeth I. [Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 14, p. 6724 - 6731]
[8]Location in patent: scheme or table Chhabria, Mahesh T.; Suhagia, Bhanubhai N.; Brahmkshatriya, Pathik S.; Raval, Priyesha M. [Arzneimittel-Forschung/Drug Research, 2011, vol. 61, # 8, p. 452 - 457]
[9]Current Patent Assignee: AMITECH THERAPEUTIC SOLUTIONS - US9212151, 2015, B2 Location in patent: Page/Page column 84-85
[10]Mihailović, Nevena; Marković, Violeta; Matić, Ivana Z.; Stanisavljević, Nemanja S.; Jovanović, Živko S.; Trifunović, Snežana; Joksović, Ljubinka [RSC Advances, 2017, vol. 7, # 14, p. 8550 - 8560]
[11]Lin, Hua; Doebelin, Christelle; Patouret, Rémi; Garcia-Ordonez, Ruben D.; Ra Chang, Mi; Dharmarajan, Venkatasubramanian; Bayona, Claudia Ruiz; Cameron, Michael D.; Griffin, Patrick R.; Kamenecka, Theodore M. [Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 8, p. 1313 - 1319]
[12]Mai, Hengtang; Wang, Yu; Li, Shuang; Jia, Ruizhen; Li, Sixian; Peng, Qian; Xie, Yan; Hu, Xiang; Wu, Song [Chemical Communications, 2019, vol. 55, # 51, p. 7374 - 7377]
[13]Fallah, Akram; Mohanazadeh, Farajollah; Safavi, Maliheh [Medicinal Chemistry Research, 2020, vol. 29, # 3, p. 341 - 355]
[14]Maniak, Halina; Talma, Michał; Giurg, Mirosław [International Journal of Molecular Sciences, 2021, vol. 22, # 22]
  • 6
  • [ 67-64-1 ]
  • [ 5818-06-4 ]
  • [ 40051-75-0 ]
YieldReaction ConditionsOperation in experiment
In isopropyl alcohol
In hexane at 65℃; for 12h; Reduction of Hydrazides General procedure: Various commercially available hydrazides (5a-n) were poured into a solution of acetone and hexane and stirred for 5 minutes. The mixture was refluxed for 12 hours at 65 C. The mixture was then cooled in ice bath to get solid precipitates and filtered to afford white solid which was washed several times with hexane. Then the corresponding hydrazides (6a-n) were shifted in methanol and stirred for 20 minutes. Sodium cyanoborohydride and acetic acid were added to this mixture and stirred for 18hrs at RT. After completion of reaction; saturated sodium bicarbonate solution was added to mixture till pH reach ~7. The mixture was extracted with ethyl acetate and water and dried over by MgSO4. After evaporation under vacuum, the mixture purified using column chromatography using n-Hexane: EtOAc:MeOH=6:3:1 as eluting system. All hydrazide derivatives were obtained coloured solids with yields were ranging from 85 to 100%.
  • 7
  • [ 5818-06-4 ]
  • [ 3788-94-1 ]
  • 2-[1-[N'-(3-Hydroxy-benzoyl)-hydrazino]-meth-(Z)-ylidene]-3-oxo-butyric acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% In ethanol Heating;
  • 8
  • [ 107-13-1 ]
  • [ 5818-06-4 ]
  • N-(2-cyanoethyl)-3-hydroxybenzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% In ethanol for 48h; Heating;
  • 9
  • [ 5818-06-4 ]
  • [ 129-64-6 ]
  • N-(m-hydroxybenzoylamino)bicyclo[2.2.1]hept-2-ene-endo,endo-5,6-dicarboximide [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With sulfuric acid In ethanol Heating;
  • 10
  • [ 78-39-7 ]
  • [ 5818-06-4 ]
  • [ 79463-11-9 ]
  • [ 1000002-31-2 ]
YieldReaction ConditionsOperation in experiment
1: 72.8% 2: 23.7% at 150℃; for 22h; 7 EXAMPLE 73-(5-Methyl-[1,3,4]oxadiazol-2-yl)-phenol; Mixture of 3-hydroxybenzoic hydrazide (0.91 g, 6 mmol) (Aldrich) and triethyl orthoacetate (4.5 mL, 24 mmol) (Aldrich) was heated in a 150° C. bath in a sealed pressure reactor for 22 hours. After cooling to room temperature, mixture was concentrated and residue purified by flash chromatography (Biotage 40 L, ethyl acetate-hexanes 1:1 as solvent) to give 2 products. The higher Rf material was recrystallized from dichloromethane-hexanes to give 2-(3-ethoxy-phenyl)-5-methyl-[1,3,4]oxadiazole as white crystals (Yield 0.29 g, 23.7%). The lower Rf material was recrystallized from dichloromethane-hexanes to give 3-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenol as white crystals. (Yield 0.77 g, 72.8%).
  • 11
  • [ 5818-06-4 ]
  • [ 79463-12-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 86 percent / 22 h / Heating 2: 53 percent / NaH / dimethylsulfoxide / 7 h / Ambient temperature
  • 12
  • [ 5818-06-4 ]
  • [ 118778-73-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 24 percent / propan-1-ol / 22 h / Heating 2: 78 percent / NaH / dimethylsulfoxide / 7 h / Ambient temperature
  • 13
  • [ 5818-06-4 ]
  • [ 79463-35-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 86 percent / 22 h / Heating 2: 53 percent / NaH / dimethylsulfoxide / 7 h / Ambient temperature 3: 87 percent / ethanol / 17 h / Heating
  • 14
  • [ 5818-06-4 ]
  • [ 118778-77-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 89 percent / 22 h / Heating 2: 69 percent / NaH / dimethylsulfoxide / 7 h / Ambient temperature 3: 73 percent / ethanol / 17 h / Heating
  • 15
  • [ 5818-06-4 ]
  • [ 79463-27-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 89 percent / 22 h / Heating 2: 69 percent / NaH / dimethylsulfoxide / 7 h / Ambient temperature 3: 72 percent / ethanol / 17 h / Heating
  • 16
  • [ 5818-06-4 ]
  • [ 118778-80-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 86 percent / 22 h / Heating 2: 53 percent / NaH / dimethylsulfoxide / 7 h / Ambient temperature 3: ethanol / 17 h / Heating
  • 17
  • [ 870615-64-8 ]
  • [ 5818-06-4 ]
  • 2-[1-(3-hydroxy-phenyl)-5-oxo-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-isopropyl-N-phenyl-acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetic acid at 120℃; for 3h; 12 Preparation of 2-[1-(3-Hydroxy-Phenyl)-5-oxo-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-isopropyl-N-phenyl-acetamide To a solution of 2-(4-ethoxy-2-oxo-2,3-dihydro-benzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-phenyl-acetamide (Preparation 5(B) (177 mg, 0.466 mmol) in glacial acetic acid (4 mL) was added 3-hydroxy benzhydrazide (90 mg, 0.591 mmol). The reaction was heated to 120° C. for 3 hours, was cooled to room temperature, and was concentrated in vacuo. The residue was triturated with 50% Et2O in hexanes and the solids were filtered. The solids were dissolved in CH2Cl2 and the organic solution was washed with aqueous NaHCO3, dried (MgSO4) and concentrated to provide 244 mg of 2-[1-(3-hydroxy-phenyl)-5-oxo-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-isopropyl-N-phenyl-acetamide. 1H NMR (CD3OD) δ7.74 (s, 2H), 7.56-7.18 (m, 10H), 6.91 (m, 1H), 4.86 (m, 1H), 4.30-4.10 (m, 2H), 3.98 (d, 1H), 3.71 (d, 1H), 1.06 (m, 6H).
  • 18
  • [ 877874-55-0 ]
  • [ 5818-06-4 ]
  • [ 877874-89-0 ]
YieldReaction ConditionsOperation in experiment
31.3% With pyridine for 18h; Heating / reflux; 56 -hydroxybenzoic acid hydrazide (2.98 g, 19.58 mmol) and S-methyl N-[4-chloro-3-(trifluoromethyl)phenyl]isothiourea hydroiodide (7.78 g, 19.63mmol) were suspended in 40 mL of anhydrous pyridine. The reaction mixture was refluxed for 18 hours, during which time it changed color from yellow into dark-red. Then it was cooled down to ambient temperature and poured with stirring into 250 mL of ice-water. The aqueous solution was decanted and the oily residue was purified by silica gel chromatography on Isco column using 0 => 50 % gradient of ethyl acetate in hexane. Solvent was removed in vacuo to give the title product as a white solid (2.176 g). 31.3 % yield.; ESI-MS: [M+H]+ 355.1, 356.8,. *H NMR (DMSO-d6): 5 6.88-6.90 (dq, Jj = 7.9 Hz, Ji« 0.9 Hz, 1H), 7.31-7.34 (t, J= 7.9 Hz, 1H), 7.35-7.39 (m, 2H), 7.54-7.56 (d, /= 8.8 Hz, 1H), 7.74-7.76 (dd, Jj = 8.8 Hz, J2= 2.7 Hz, 1H), 8.23-8.24 (d, J= 2.7 Hz, 1H), 9.79 (s, 1H), 9.87 (s, 1H), 13.86 (s, 1H).
  • 19
  • [ 5470-96-2 ]
  • [ 5818-06-4 ]
  • 3-hydroxybenzoic acid (2-quinolinylmethylene)hydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
3.43 gm (56%) In methanol Preparation of 3-hydroxybenzoic acid (2-quinolinylmethylene)hydrazide, Compound 20 Preparation of 3-hydroxybenzoic acid (2-quinolinylmethylene)hydrazide, Compound 20 A mixture of 3.3 gm (0.021 mole) of 2-quinolinecarboxaldehyde, 3.20 gm (0.021 mole) of m-hydroxybenzhydrazide and 100 ml of methanol is refluxed for 8 hrs. The solvent is evaporated in vacuo to give a solid. The crude product is crystallized from ethanol/DMF/water to yield 3.43 gm (56%) of the title compound, having a melting point of >272° C. (decomp.). Calcd: C, 70.09; H, 4.50; N, 14.42. Found: C, 69.57; H, 4.51; N, 14.46.
  • 20
  • [ 5470-96-2 ]
  • [ 5818-06-4 ]
  • [ 99-06-9 ]
YieldReaction ConditionsOperation in experiment
3.43 gm (56%) In methanol Procedure 8 Preparation of 3-hydroxybenzoic acid (2-quinolinylmethylene-hydrazide, Compound 20 Procedure 8 Preparation of 3-hydroxybenzoic acid (2-quinolinylmethylene-hydrazide, Compound 20 A mixture of 3.3 gm (0.021 mole) of 2-quinolinecarboxaldehyde, 3.20 gm (0.021 mole) of m-hydroxybenzhydrazide and 100 ml of methanol is refluxed for 8 hrs. The solvent is evaporated in vacuo to give a solid. The crude product is crystallized from ethanol/DMF/water to yield 3.43 gm (56%) of the title compound, having a melting point of >272°C (decomp.). Calcd: C, 70.09; H, 4.50; N, 14.42. Found: C, 69.57; H, 4.51; N, 14.46.
  • 21
  • [ 100-83-4 ]
  • [ 5818-06-4 ]
  • [ 897753-98-9 ]
YieldReaction ConditionsOperation in experiment
70% Stage #1: meta-hydroxybenzaldehyde With acetic acid In ethanol at 20℃; for 0.166667h; Stage #2: 3-hydroxybenzoic hydrazide In ethanol at 20℃; for 12h; Synthesis of resveratrol derivatives 2a-f General procedure: To a solution of hydroxy-benzaldehyde (ortho, meta, para) (1mmol) in ethanol (10mL) was added acetic acid as catalyst and stirring was maintained during 10 minutes. Hydroxy-benzhydrazide (meta, para) (1mmol) was added and the reaction was stirred for 12 hours under room temperature. After, portions of ice was added into reaction to obtain a white solid, which was washed with cold water, filtered and dried under bench vacuum flow.
With formic acid In dimethyl sulfoxide
  • 22
  • [ 698-63-5 ]
  • [ 5818-06-4 ]
  • C12H9N3O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% In ethanol; water Heating;
  • 23
  • [ 4521-33-9 ]
  • [ 5818-06-4 ]
  • C12H9N3O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% In ethanol; water Heating;
  • 24
  • [ 588671-28-7 ]
  • [ 5818-06-4 ]
  • C27H27N3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With acetic acid In ethanol for 1h; Heating;
  • 25
  • [ 492-88-6 ]
  • [ 5818-06-4 ]
  • N'-[(2-hydroxy-3-ethoxy)benzylidene]-3-hydroxybenzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% In methanol
  • 26
  • [ 148-53-8 ]
  • [ 5818-06-4 ]
  • N'-[(2-hydroxy-3-methoxy)benzylidene]-3-hydroxybenzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% In methanol
  • 27
  • [ 19652-32-5 ]
  • [ 5818-06-4 ]
  • [ 1204206-09-6 ]
YieldReaction ConditionsOperation in experiment
90% In methanol at 20℃;
  • 28
  • [ 75-15-0 ]
  • [ 5818-06-4 ]
  • [ 299465-12-6 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide In ethanol at 80℃; for 12h;
  • 29
  • [ 75-15-0 ]
  • [ 5818-06-4 ]
  • [ 74-88-4 ]
  • [ 380639-34-9 ]
YieldReaction ConditionsOperation in experiment
87% Stage #1: carbon disulfide; 3-hydroxybenzoic hydrazide With potassium hydroxide In ethanol; water at 20℃; for 0.25h; Stage #2: methyl iodide In ethanol; water Cooling;
  • 30
  • [ 75-15-0 ]
  • [ 5818-06-4 ]
  • C8H7N2O2S2(1-)*K(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-hydroxybenzoic hydrazide With potassium hydroxide In methanol for 0.25h; Stage #2: carbon disulfide at 20 - 25℃; for 3h;
  • 31
  • [ 99-06-9 ]
  • [ 5818-06-4 ]
YieldReaction ConditionsOperation in experiment
85% Stage #1: 3-Carboxyphenol With sulfuric acid In ethanol for 6h; Reflux; Stage #2: With hydrazine hydrate; sodium hydrogencarbonate; acetic acid Reflux;
Multi-step reaction with 2 steps 1: sulfuric acid / Reflux 2: hydrazine hydrate / Reflux
Multi-step reaction with 2 steps 1: sulfuric acid / 0.32 h / Reflux; Microwave irradiation 2: hydrazine hydrate / ethanol / 0.25 h / Reflux; Microwave irradiation
Multi-step reaction with 2 steps 1: sulfuric acid / water / 6 h / Reflux 2: hydrazine hydrate / water; ethanol / Reflux
Multi-step reaction with 2 steps 1: sulfuric acid / 5 h / Reflux 2: hydrazine hydrate / ethanol / 12 h / Reflux
Multi-step reaction with 2 steps 1: Heating; Acidic conditions 2: hydrazine / ethanol / Heating
Multi-step reaction with 2 steps 1: sulfuric acid / Reflux 2: hydrazine hydrate / Reflux
Multi-step reaction with 2 steps 1: thionyl chloride / 48 h / 0 - 65 °C 2: hydrazine hydrate / methanol / 48 h / Reflux
Multi-step reaction with 2 steps 1: sulfuric acid / Reflux 2: hydrazine hydrate / ethanol / Reflux
Multi-step reaction with 2 steps 1: sulfuric acid / Reflux 2: H4N2*5H2O / ethanol / Reflux
Multi-step reaction with 2 steps 1: thionyl chloride / 12 h / Reflux 2: hydrazine hydrate / ethanol / 12 h / Reflux

Reference: [1]Nisa, Mehr-un; Munawar, Munawar A.; Iqbal, Amber; Ahmed, Asrar; Ashraf, Muhammad; Gardener, Qurra-tul-Ann A.; Khan, Misbahul A. [European Journal of Medicinal Chemistry, 2017, vol. 138, p. 396 - 406]
[2]Chhabria, Mahesh T.; Suhagia, Bhanubhai N.; Brahmkshatriya, Pathik S.; Raval, Priyesha M. [Arzneimittel-Forschung/Drug Research, 2011, vol. 61, # 8, p. 452 - 457]
[3]Zaheer, Muhammad; Zia-Ur-Rehman, Muhammad; Rahman, Salma; Ahmed, Naveed; Chaudhary, Muhammad Nawaz [Journal of the Chilean Chemical Society, 2012, vol. 57, # 4, p. 1492 - 1496]
[4]Mehr-Un-Nisa; Munawar, Munawar A.; Chattha, Fauzia A.; Kousar, Samina; Munir, Jawaria; Ismail, Tayaba; Ashraf, Muhammad; Khan, Misbahul A. [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 17, p. 6014 - 6024]
[5]Mihailović, Nevena; Marković, Violeta; Matić, Ivana Z.; Stanisavljević, Nemanja S.; Jovanović, Živko S.; Trifunović, Snežana; Joksović, Ljubinka [RSC Advances, 2017, vol. 7, # 14, p. 8550 - 8560]
[6]Kaproń, Barbara; Łuszczki, Jarogniew J.; Siwek, Agata; Karcz, Tadeusz; Nowak, Gabriel; Zagaja, Mirosław; Andres-Mach, Marta; Stasiłowicz, Anna; Cielecka-Piontek, Judyta; Kocki, Janusz; Plech, Tomasz [Bioorganic Chemistry, 2020, vol. 94]
[7]Fallah, Akram; Mohanazadeh, Farajollah; Safavi, Maliheh [Medicinal Chemistry Research, 2020, vol. 29, # 3, p. 341 - 355]
[8]Giurg, Mirosław; Maniak, Halina; Matyja, Konrad; Talma, Michał; Trusek, Anna [Molecules, 2020, vol. 25, # 5]
[9]Dige, Nilam C.; Hassan, Mubashir; Lee, Ki Hwan; Mahajan, Prasad G.; Raza, Hussain; Seo, Sung-Yum; Vanjare, Balasaheb D. [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2020, vol. 241]
[10]Babu, Bathini Nagendra; Devi, Ganthala Parimala; Kamal, Ahmed; Kumar, C. Ganesh; Rani Routhu, Sunitha; Shareef, Mohd Adil [RSC Medicinal Chemistry, 2020, vol. 11, # 10, p. 1178 - 1184]
[11]Yamazaki, Diego A.S.; Rozada, Andrew M.F.; Baréa, Paula; Reis, Elaine C.; Basso, Ernani A.; Sarragiotto, Maria Helena; Seixas, Flávio A.V.; Gauze, Gisele F. [Bioorganic and Medicinal Chemistry, 2021, vol. 32]
  • 32
  • [ 113-24-6 ]
  • [ 5818-06-4 ]
  • [ 1391436-68-2 ]
YieldReaction ConditionsOperation in experiment
87% In methanol; water for 2h; Reflux;
  • 35
  • [ 490-78-8 ]
  • [ 5818-06-4 ]
  • [ 444767-48-0 ]
YieldReaction ConditionsOperation in experiment
79% In ethanol Reflux;
  • 36
  • [ 24683-21-4 ]
  • [ 5818-06-4 ]
  • [ 1421621-62-6 ]
YieldReaction ConditionsOperation in experiment
79% In ethanol for 0.383333h; Reflux; Microwave irradiation;
  • 37
  • [ 23911-26-4 ]
  • [ 5818-06-4 ]
  • C28H35N7O12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
87.8% With pyridine In water at 20℃; for 24h;
  • 38
  • [ 17422-74-1 ]
  • [ 5818-06-4 ]
  • [ 1436436-00-8 ]
YieldReaction ConditionsOperation in experiment
80% With acetic acid In ethanol at 20℃; for 6h; General procedure: to a mixture solution of 3-formylchromone d1 (174 mg, 1 mmol) and benzohydrazide e1 (136 mg, 1 mmol) in 25 mL ethanol was added three drops of acetic acid with stirring for 6 h at room temperature. Insoluble solid was gradually generated, then filtered and washed several times with ethanol. After drying, pure target compound f1 was afforded (227 mg, yield 78%).
  • 39
  • 3-[5-oxo-4-(phenylsulfonyl)-1,2,5-oxadiazol-3-yl]oxy}benzaldehyde [ No CAS ]
  • [ 5818-06-4 ]
  • 3-hydroxy-N'-[(1E)-(3-[5-oxido-4-(phenylsulfonyl)-1,2,5-oxadiazol-3-yl]oxy}phenyl)methylene]benzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With acetic acid In ethanol at 20℃; for 12h; Inert atmosphere;
  • 40
  • 4-[5-oxo-4-(phenylsulfonyl)-1,2,5-oxadiazol-3-yl]oxy}benzaldehyde [ No CAS ]
  • [ 5818-06-4 ]
  • 3-hydroxy-N'-[(1E)-(4-[5-oxido-4-(phenylsulfonyl)-1,2,5-oxadiazol-3-yl]oxy}phenyl)methylene]benzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With acetic acid In ethanol at 20℃; for 12h; Inert atmosphere;
  • 41
  • C39H60O8 [ No CAS ]
  • [ 5818-06-4 ]
  • C46H66N2O9 [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% With phosphotungstic acid In N,N-dimethyl-formamide at 60℃; for 4h; 3.6.1. Brevenal Derivatives General procedure: In a typical reaction, brevenal was dissolved in DMF and the hydrazide (2 eq) was added, followed by addition of a catalytic amount of tungstophosphoric acid. The reaction mixture was heated at 60 °C for 4 h. The solvents were evaporated under vacuum and the residue was taken up in methanol. The mixture was filtered through a 0.2 μm nylon filter and subjected to purification by HPLC. Desired products were positively identified by HRMS mass spectrometry and NMR. Spectroscopic data collected for all compounds can be found in the supplementary data document.
  • 42
  • [ 2284-20-0 ]
  • [ 5818-06-4 ]
  • 2-(3-hydroxybenzoyl)-N-(4-methoxyphenyl)hydrazine-1-carbothioamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% In ethanol for 0.25h; Reflux;
78% for 2h; 4.3.1 General procedure for synthesis of the thiosemicarbazide derivatives (1a-i) General procedure: According to a previously reported method [17], a mixture of the appropriate hydrazide (5mmol) and 1-isothiocyanato-4-methoxybenzene (5mmol) in 20mL anhydrous ethanol or methanol was stirred at room temperature or with heat for approximately 2h. The progress of the reaction was monitored by thin layer chromatography using silica gel plates. When the reaction was completed, the mixture was cooled and filtered. The precipitate was washed with cold ethanol and dried to obtain the desired product. For more details, please refer to 1a[32], 1b[33], 1c[34], 1d[35], 1e[35], 1f[35], 1g[34], 1h[36], and 1i[37], respectively.
  • 43
  • [ 6590-94-9 ]
  • [ 5818-06-4 ]
  • 4-(3,4-dichlorophenyl)-1-(3-hydroxybenzoyl)-3-thiosemicarbazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% In ethanol for 0.25h; Reflux;
47% In methanol at 20℃; for 24h; 5.1.2. General procedure for the preparation of thiosemicarbazides(3, 14-48 and 51-52) General procedure: A series of thiosemicarbazides 3, 14-48 and 51-52 were preparedaccording to a procedure adapted from the literature [40,41]by adding an isothiocyanate (1 equiv) dropwise to a solution ofbenzohydrazide (1 equiv) in methanol. The reaction mixture wasstirred at room temperature and its progress was followed by TLC.The precipitate was then collected by filtration, washed with coldethanol and then recrystallized from ethanol as many times asnecessary to obtain a pure product.
  • 44
  • [ 5818-06-4 ]
  • [ 98041-69-1 ]
  • 4-(4-bromo-2-chlorophenyl)-1-(3-hydroxybenzoyl)thiosemicarbazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% In ethanol for 0.25h; Reflux;
  • 45
  • [ 19241-37-3 ]
  • [ 5818-06-4 ]
  • 4-(3-chloro-4-methylphenyl)-1-(3-hydroxybenzoyl)thiosemicarbazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% In ethanol for 0.25h; Reflux;
  • 46
  • [ 5818-06-4 ]
  • [ 23163-86-2 ]
  • 4-[4-chloro-3-(trifluoromethyl)phenyl]-1-(3-hydroxybenzoyl)thiosemicarbazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% In ethanol for 0.25h; Reflux;
  • 47
  • [ 532-55-8 ]
  • [ 5818-06-4 ]
  • 4-benzoyl-1-(3-hydroxybenzoyl)thiosemicarbazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% In ethanol for 0.25h; Reflux;
  • 48
  • [ 622-78-6 ]
  • [ 5818-06-4 ]
  • 4-benzyl-1-(3-hydroxybenzoyl)thiosemicarbazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% In ethanol for 0.25h; Reflux;
  • 49
  • [ 2740-88-7 ]
  • [ 5818-06-4 ]
  • 4-(4-fluorobenzyl)-1-(3-hydroxybenzoyl)thiosemicarbazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% In ethanol for 0.25h; Reflux;
  • 50
  • [ 3694-57-3 ]
  • [ 5818-06-4 ]
  • 1-(3-hydroxybenzoyl)-4-(4-methoxybenzyl)thiosemicarbazide [ No CAS ]
  • 52
  • [ 5818-06-4 ]
  • [ 219861-08-2 ]
  • (S)-3-(5-{1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-yl}-4H-1,2,4-triazol-3-yl)phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With potassium carbonate In butan-1-ol at 150℃; 6 Synthesis of escitalopram triazoles General procedure: The triazoles of escitalopram (60-88) were synthesized byfollowing a reported method for triazole formation.25 A mixtureof a benzohydrazide (33 mmol), escitalopram (59-oxalate,10 mmol) and K2CO3 (0.5 mmol) in n-butanol (2 mL) was heatedat 150 C for 5-6 h. The reaction was monitored with TLC. Afterthe completion of the reaction, the solvent was removed underreduced pressure. Finally, the triazole derivatives of escitalopram(60-88) were purified with column chromatography using solventsystem CH3OH/CH3Cl = 60:40 and finally with preparative thinlayer chromatography.
  • 53
  • [ 5818-06-4 ]
  • (E)-3-((2-(3-((2-acetoxybenzoyl)oxy)benzoyl)hydrazono)methyl)-4-methyl-1,2,5-oxadiazole 5-oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrogenchloride / ethanol; water / 15 h / 25 °C 2: dicyclohexyl-carbodiimide; dmap / dichloromethane / 15 h / Inert atmosphere
  • 54
  • [ 123953-16-2 ]
  • [ 5818-06-4 ]
  • 3-((2-(3-hydroxybenzoyl)hydrazono)methyl)-4-methyl-1,2,5-oxadiazole 5-oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
47.2% With hydrogenchloride In ethanol; water at 25℃; for 15h; 3.2.1. General Procedures for the Preparation of Intermediates (3a,b, 8a,b and 13a,b) General procedure: The corresponding aromatic aldehyde (2, 7, or 12) (2 mmol) was added to a solution of previouslyselected 3- or 4-hydroxybenzhydrazide derivatives (2 mmol) in 15 mL of absolute ethanol, in thepresence of a catalytic amount of 37% hydrochloric acid (80 μL). The reaction was stirred for 15 h atroom temperature and monitored by TLC. Afterwards, the solvent was partially concentrated atreduced pressure, and the resulting mixture was poured into cold water. The precipitate was collectedby filtration, washed with cold ethanol, and dried under vacuum to give the intermediates containingthe N-acyl hydrazone subunit (3a,b, 8a,b and 13a,b). If necessary, the compounds can be purified bycolumn chromatography (flash silica, eluent: 70% ethyl acetate; 30% hexane). 3-((2-(3-Hydroxybenzoyl)hydrazono)methyl)-4-methyl-1,2,5-oxadiazole 2-oxide (3a): Pale yellow solid.Yield: 47.2%, mp: 225-227 °C. IR νmax (cm-1; KBr pellets): 3414 (O-H), 1635 (C=O amide), 1616(C=N), 1458 (C-H methyl), 1300 (N-O) and 800 (C-H aromatic). 1H-NMR (300 MHz, DMSO-d6) δ:9.80 (1H; O-H), 8.46 (1H; s; C-Himine), 7.36 (1H; t; J = 7.9 Hz; C-Haromatic), 7.34 (1H; t; J = 7.9 Hz; C-Haromatic), 7.31 (1H; t; J = 7.9 Hz; C-Haromatic), 7.01 (1H; d; C-Haromatic), 7 (1H; N-Hamide), 2.39 (3H; s;C-Hmethyl) ppm. 13C-NMR (75 MHz, DMSO-d6) δ: 137.7, 129.5, 119.2, 118.1, 114.7, 9.0 ppm.Analysis calculated for C11H10N4O4: C, 50.38; H, 3.84; N, 21.37. Found: C, 50.11; H, 3.82; N, 21.21.Mass calculated: m/z 262.07; Found Low-resolution mass spectrometry (LRMS): m/z 263.07 [M + H]+.
  • 55
  • [ 135733-34-5 ]
  • [ 5818-06-4 ]
  • 3-((2-(3-hydroxybenzoyl)hydrazono)methyl)-4-phenyl-1,2,5-oxadiazole 2-oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
39.1% With hydrogenchloride In ethanol; water at 25℃; for 15h; 3.2.1. General Procedures for the Preparation of Intermediates (3a,b, 8a,b and 13a,b) General procedure: The corresponding aromatic aldehyde (2, 7, or 12) (2 mmol) was added to a solution of previouslyselected 3- or 4-hydroxybenzhydrazide derivatives (2 mmol) in 15 mL of absolute ethanol, in thepresence of a catalytic amount of 37% hydrochloric acid (80 μL). The reaction was stirred for 15 h atroom temperature and monitored by TLC. Afterwards, the solvent was partially concentrated atreduced pressure, and the resulting mixture was poured into cold water. The precipitate was collectedby filtration, washed with cold ethanol, and dried under vacuum to give the intermediates containingthe N-acyl hydrazone subunit (3a,b, 8a,b and 13a,b). If necessary, the compounds can be purified bycolumn chromatography (flash silica, eluent: 70% ethyl acetate; 30% hexane).
  • 56
  • [ 57948-15-9 ]
  • [ 5818-06-4 ]
  • (E)-6-((2-(3-hydroxybenzoyl)hydrazono)methyl)benzo[c][1,2,5]oxadiazole 1-oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With acetic acid In ethanol at 20℃; for 12h;
50.9% With hydrogenchloride In ethanol; water at 25℃; for 15h; 3.2.1. General Procedures for the Preparation of Intermediates (3a,b, 8a,b and 13a,b) General procedure: The corresponding aromatic aldehyde (2, 7, or 12) (2 mmol) was added to a solution of previouslyselected 3- or 4-hydroxybenzhydrazide derivatives (2 mmol) in 15 mL of absolute ethanol, in thepresence of a catalytic amount of 37% hydrochloric acid (80 μL). The reaction was stirred for 15 h atroom temperature and monitored by TLC. Afterwards, the solvent was partially concentrated atreduced pressure, and the resulting mixture was poured into cold water. The precipitate was collectedby filtration, washed with cold ethanol, and dried under vacuum to give the intermediates containingthe N-acyl hydrazone subunit (3a,b, 8a,b and 13a,b). If necessary, the compounds can be purified bycolumn chromatography (flash silica, eluent: 70% ethyl acetate; 30% hexane).
  • 57
  • [ 5818-06-4 ]
  • [ 1840-19-3 ]
  • C15H10F3N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-hydroxybenzoic hydrazide; 1-isothiocyanato-3-trifluoromethyl-benzene In tetrahydrofuran; N,N-dimethyl-formamide; toluene at 80℃; for 0.5h; Inert atmosphere; Stage #2: With dicyclohexyl-carbodiimide In tetrahydrofuran; N,N-dimethyl-formamide; toluene at 80℃; 2.4 Step-4: Preparation of the scaffold To a suspension of methyl 3-hydroxy benzohydrazide (1 g, 6.5 mmol) in THF:Toluene:DMF (5 mL) each was added 1-Isothiocyanato-3-(trifluoromethyl)benzene (1.33 g, 6.5 mmol) under N2↑ atmosphere at room temperature. After complete addition of isothiocyanate reaction mixture was stirred at 80° C. for 30 min. Then DCC (1.49 g, 7.23 mmol) was added and reaction mixture was stirred at 80° C. for 5-6 h. When TLC (mobile phase-5% methanol in chloroform, Rf. S.M.-0. 0.30, product-0.5) showed absence of starting material and formation of product, the reaction mixture was cooled to room temperature; water was added and the reaction mixture was extracted with ethyl acetate (3×50 mL). The combined organic layer was dried over Na2SO4 and concentrated in vacuo to give the crude product. This was purified by column chromatography to afford desired product (750 mg). (0364) Yield: 35.5% (0365) HPLC Purity: 90.6% (0366) 1H NMR: Consistent with structure (0367) LCMS: MH+322 (Mol. Wt 321)
  • 58
  • [ 65069-76-3 ]
  • [ 5818-06-4 ]
  • C15H11F3N4O [ No CAS ]
YieldReaction ConditionsOperation in experiment
42.35% In pyridine at 100℃; Inert atmosphere; 1.6 Step-6: Preparation of the scaffold-method 1 To a suspension of methyl S-Methyl-3-(trifluoromethyl)phenylisothiourea hydroiodide (5 g, 13.81 mmol) in anhydrous pyridine (30 mL) was added 3-hydroxy benzohydrazide (2.32 g, 15.26 mmol) under N2 atmosphere. After complete addition of hydrazide, the reaction mixture was stirred at 100° C. for 10-12 h. When TLC (mobile phase-10% methanol in chloroform, Rf. S.M.-0. 20, product-0.4) showed absence of starting material, the reaction mixture was cooled to room temperature and the pyridine was concentrated under vacuum to get the crude product (yellow oil). This was purified by column chromatography to afford the desired scaffold in a pure form. (0347) Yield: 42.35% (0348) HPLC Purity: 98.08% (0349) 1H NMR: Consistent with structure (0350) LCMS: MH+321 (Mol. Wt 320)
  • 59
  • [ 5818-06-4 ]
  • [ 43100-24-9 ]
YieldReaction ConditionsOperation in experiment
With [bis(acetoxy)iodo]benzene In methanol
  • 60
  • 1-[4-hydroxy-3-(2-methyl-benzofuran-5-yl)phenyl]-2-propanone [ No CAS ]
  • [ 5818-06-4 ]
  • 1-[4-hydroxy-3-(2-methylbenzofuran-5-yl)phenyl]-2-propanone 3-hydroxybenzoylhydrazone [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With acetic acid In ethanol for 5h; Reflux; General procedure for the synthesis of substitutedbenzoylhydrazone (7-23) General procedure: To a solution of 5 (0.5 mmol) and substituted benzoylhydrazide (0.55 mmol) in EtOH(20 ml) acetic acid (0.2 ml) was added. After stirred and refluxed for 5 h, the reactionwas concentrated, poured into saturated salt water, shocked, and placed until precipitation.Then the precipitate was separated by filtration, washed with water, and driedto afford substituted benzoylhydrazone (7-23).
67.6% With acetic acid In ethanol for 2h; Reflux; 12 Example 12 1- [4-hydroxy-3- (2-methyl-benzofuran-5-yl) phenyl] -3-hydroxy-benzoyl-2-propanone hydrazone 0.5mmol1- [4- hydroxy-3- (2-methyl-benzofuran-5-yl) phenyl] -2-propanone, 0.55mmol3--hydroxybenzoic acid hydrazide, dissolved with 20ml of ethanol was added 0.2ml of glacial acetic acid after reflux for 2h, add 50ml ethanol distilled under reduced pressure to a residual solution 5ml, TLC monitoring completion of the reaction; adding water, fully shock, standing, the precipitated solid was filtered, the filter cake washed with water and washed with 50% ethanol and dried to give a white solid 1 - [4-hydroxy-3- (2-methyl-benzofuran-5-yl) phenyl] -3-hydroxy-2-propanone benzoylhydrazone, yield 67.6%
  • 61
  • [ 65-22-5 ]
  • [ 5818-06-4 ]
  • C15H13N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With acetic acid; In methanol; at 60℃; for 4h; Compound 3 was obtained with good yield by condensation of <strong>[65-22-5]pyridoxal hydrochloride</strong> with 3-hydroxybenzoic acid hydrazide. A solution of 0.152 g (1 mmol) of 3-hydroxybenzoic acid hydrazide in methanol (5 mL) was prepared. Parallelly, 0.204 g (1 mmol) of <strong>[65-22-5]pyridoxal hydrochloride</strong> was dissolved in the same solvent (5 mL).The resulting solution was added slowly to the hydrazide under constant stirring. To the obtained pale-yellow mixture were added few drops of glacial acetic acid. The mixture was stirred at 60 C for 4 h until its colour changed to intense yellow. Further, it was concentrated to half of the initial volume when the fine yellow mass was formed. The resulting solid compound was filtered, washed with alcohol and dried under vacuum. Reaction yield: 71 %. ESI-MS(positive mode, MeOH:H2O) m/z: [LNa]? calculated forC15H15N3O4Na 324.3, found 324.2.
  • 62
  • [ 98-88-4 ]
  • [ 5818-06-4 ]
  • [ 162892-78-6 ]
YieldReaction ConditionsOperation in experiment
74% In tetrahydrofuran at 20℃; for 6h;
  • 63
  • [ 606-23-5 ]
  • [ 5818-06-4 ]
  • (E)-3-hydroxy-N'-(3-oxo-2,3-dihydro-1H-inden-1-ylidene)benzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With acetic acid In ethanol for 2h; Reflux; 2 4.4.5. Synthesis of compound 9 General procedure: To a solution of 8 (1.1 mmol) in ethanol (5 mL) were added thiosemicarbazide (1.0 mmol) and acetic acid (0.1 mmol). After stirring at reflux for about 2-4 h, the reaction was cooled to room temperature and the formed solid was filtered off, dried and recrystallized to afford 9.
  • 64
  • [ 5818-06-4 ]
  • 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxylic acid [ No CAS ]
  • N'-(3-hydroxybenzoyl)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% Stage #1: 3-hydroxybenzoic hydrazide; 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxylic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In N,N-dimethyl-formamide for 0.333333h; Stage #2: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 1h; 4.4.1 General procedure General procedure: 5-(Aroylhydrazinocarbonyl)escitalopram (58-84) were synthesized by the coupling reaction conditions mostly used in peptide synthesis [19]. 5-Carboxyescitalopram (3, 0.001mmol) and benzohydrazide (31, 0.001mmol) were dissolved in DMF (15mL). After five minutes stirring, HBTU (0.0012mmol) was incorporated and stirred for 20min. Then DIEA (0.002mmol) was added and stirred for 1h. Saturated solution of NH4Cl (1×10mL) was added into the reaction mixture and extracted with ethyl acetate (3×10mL). The ethyl acetate layer was washed with solution of NaHCO3 (5%, 2×10mL) followed by brine (1×10mL) and dried over anhydrous MgSO4 overnight. After the removal of ethyl acetate under reduced pressure, the residue was purified using column chromatography.
  • 65
  • [ 123-08-0 ]
  • [ 5818-06-4 ]
  • 4-hydroxybenzaldehyde-3-hydroxybenzoyl hydrazone [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% Stage #1: 4-hydroxy-benzaldehyde With acetic acid In ethanol at 20℃; for 0.166667h; Stage #2: 3-hydroxybenzoic hydrazide In ethanol at 20℃; for 12h; Synthesis of resveratrol derivatives 2a-f General procedure: To a solution of hydroxy-benzaldehyde (ortho, meta, para) (1mmol) in ethanol (10mL) was added acetic acid as catalyst and stirring was maintained during 10 minutes. Hydroxy-benzhydrazide (meta, para) (1mmol) was added and the reaction was stirred for 12 hours under room temperature. After, portions of ice was added into reaction to obtain a white solid, which was washed with cold water, filtered and dried under bench vacuum flow.
  • 66
  • 3-[5-oxo-4-(phenylsulfonyl)-1,2,5-oxadiazol-3-yl]oxy}benzaldehyde [ No CAS ]
  • [ 5818-06-4 ]
  • C22H16N4O7S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid In ethanol at 25℃; for 12h;
  • 67
  • 4-[5-oxo-4-(phenylsulfonyl)-1,2,5-oxadiazol-3-yl]oxy}benzaldehyde [ No CAS ]
  • [ 5818-06-4 ]
  • C22H16N4O7S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid In ethanol at 25℃; for 12h;
  • 68
  • [ 42248-31-7 ]
  • [ 5818-06-4 ]
  • (E)-N'-((6-chloro-4-oxo-4H-chromen-3-yl)methylene)-3-hydroxybenzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With acetic acid In ethanol at 85℃; for 5h;
77% With acetic acid In ethanol at 85℃; for 5h; 9.2 Step 2: The purified 6-chloro-3-formylchromone (Compound 35; 60 mg, 0.3 mmol) was reacted with m-Hydroxybenzohydrazide (Compound 36; 45 mg, 0.3 mmol) was reacted with Was dissolved in ethanol (10 mL) contained. Glacial acetic acid was added in a catalytic amount, and the reaction mixture was refluxed at 85 DEG C for 5 hours. Next, the reaction mixture was cooled to room temperature, the solvent was removed in vacuo, The resulting residue was purified by column chromatography to obtain the desired compound (Yield: 77%; m.p: 196-202 [deg.]
  • 69
  • [ 5818-06-4 ]
  • [ 149-73-5 ]
  • [ 5378-29-0 ]
YieldReaction ConditionsOperation in experiment
92% for 24h; Reflux; 3 Synthesis of 2- (3-hydroxyphenyl) -1,3,4-oxadiazole A mixture of methyl 3-hydroxybenzoate (6.85 g, 45.0 mmol), hydrazine hydrate (11.2 mL of 80% aqueous solution) and ethanol (60 mL) was heated under reflux for 48 hours and then cooled to room temperature. Washed with cold water and dried to give the target product 3-hydroxybenzohydrazide 4.34g, yield 63%. The resulting 3-hydroxybenzohydrazide (4.34 g, 28.5 mmol) was then mixed with trimethoxymethane (19.7 mL) and heated to reflux for 24 hours. After cooling and removal of excess trimethoxymethane under reduced pressure, the crude product was isolated and purified by silica gel column chromatography to give 4.24 g of the target product in a yield of 92%.
  • 70
  • C16H14FN3O2 [ No CAS ]
  • [ 5818-06-4 ]
  • N'-(1-(2-(4-fluorophenyl)-2-methyl-5-(pyridin-4-yl)-1,3,4-oxadiazol-3(2H)-yl)ethylidene)-3-hydroxybenzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With zinc(II) chloride In ethanol for 0.166667h; Microwave irradiation; Inert atmosphere; General procedure for the synthesis of 1-(2-(1H-indol-3-yl)-5-(pyridin-4-yl)-1,3,4-oxadiazol-3(2H)-yl)-3-(aryl)-prop-2-en-1-ones (5a-t) General procedure: A mixture of intermediate compound 1-(2-(4-fluorophenyl)-2-methyl-5-(pyridin-4-yl)-1,3,4-oxadiazol-3(2H)-yl)ethanone (4) (0.01 mol), different substituted benzohydrazide (0.01 mol) and ethanol (5 mL) was placed in a closed vessel along with catalytic amount of anhydrous ZnCl2 in it and irradiated under microwave condition with magnetic stirring for 10 min and with a maximum power of 350 W intermittently at 30 s intervals. Reaction progress was monitored by TLC and the reaction mixture was cooled and treated with chilled water. The precipitates thus obtained were filtered, washed with water and then recrystallized from absolute alcohol (99.9%) to give compounds 5a-t.
  • 71
  • [ 35272-15-2 ]
  • [ 5818-06-4 ]
  • N′-(3-hydroxybenzoyl)-2-methylthiazole-4-carbohydrazide [ No CAS ]
  • 72
  • [ 19005-93-7 ]
  • [ 5818-06-4 ]
  • (E)-N'-((1H-indol-2-yl)methylene)-3-hydroxybenzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% In ethanol for 18h; Reflux; 4.2.2. General procedure for the synthesis of hydrazones (19-21) General procedure: A mixture of indole-2-carboxaldehyde 18 (0.14 g, 1 mmol) and theappropriate hydroxybenzohydrazide (1 mmol) in EtOH (10 mL) wasrefluxed for 18 h. After cooling the formed precipitate was filtered offand purified by crystallization from the adequate solvent to give thehydrazone derivatives. (19). Yield 70%. Mp > 250 °C (EtOH). 1H NMR (DMSO-d6): δ 6.82 (s,1H, Ar), 7.00 (d, J=8.0 Hz, 2H, Ar), 7.15 (m, 2H, Ar), 7.32 (m, 2H,Ar), 7.44 (d, J=7.5 Hz, 1H, Ar), 7.55 (d, J=8.0 Hz, 1H, Ar), 8.47 (s,1H, CH), 9.75 (s, 1H, OH), 11.56 (s, 1H, NH), 11.74 (s, 1H, NH). IR(Nujol) 3331, 1655, 1596 cm-1. m/z 280 (M+H)+. Anal. Calcd forC16H13N3O2: C, 68.81; H, 4.69; N, 15.05. Found: C, 68.89; H, 4.68; N,15.01.
  • 73
  • [ 24424-99-5 ]
  • [ 5818-06-4 ]
  • C12H16N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% In methanol at 35℃; 1.4 (4) Synthesis of Compound 2c To contain 19 g (125 mmol) of 2b (for the synthesis of compound 2b, see Bioorganic & Medicinal Chemistry, 2017, 25, 3780-3791)Add 34 mL (150 mmol) of Boc anhydride to 15 mL of methanol.It was stirred at 35 ° C overnight.After the reaction, excess methanol was removed and dichloromethane was added.Stir until a white precipitate precipitates, suction filtration,Thus, 28 g of a white solid powder (2c) was obtained in a yield of 89%.
89% In methanol at 35℃;
  • 74
  • [ 17356-08-0 ]
  • [ 5818-06-4 ]
  • 3-(5-amino-1H-1,2,4-triazol-3-yl)phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With potassium carbonate; dimethyl sulfate In water at 50℃; for 20h; Green chemistry; General procedure for the preparation of 1,2,4-triazol-5(3)-amines 4a-j General procedure: A suspension of thiourea (1) (0.076 g, 1 mmol), hydrazides 3a-j (1 mmol), dimethyl sulfate (2) (0.063 g, 0.5 mmol) and potassium carbonate (0.069 g, 0.5 mmol) in 4 mL water was heated at 50 °C for 15-20 h. The reaction progress was checked with TLC. The mixture was cooled in an ice bath in order to increase in total precipitation. The solid was fltered of, washed with cold water and ethanol, and dried in an oven at 60 °C without need for further purifcation.
  • 75
  • [ 4404-45-9 ]
  • [ 5818-06-4 ]
  • 4-hexyl-1-(3-hydroxybenzoyl)thiosemicarbazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% at 110℃; for 0.0833333h; 4.1.1. Synthesis of the compounds 1-22 General procedure: Equimolar amounts of various alkyl isothiocyanates and carboxylicacid hydrazides (obtained from the respective carboxylic acids) weremixed together and heated to 110 °C until a product was formed (i.e.,for 5 min). The obtained thiosemicarbazide derivatives were washedwith diethyl ether, filtered and crystallized from anhydrous ethanol.These compounds were subsequently dissolved in 2% NaOH and heatedunder reflux for 2 h. After cooling to room temperature, the solvent wasneutralized with 3M HCl to form a solid of appropriate 4-alkyl-5-substituted-1,2,4-triazole-3-thione derivative, which was filtered, dried and crystallized from anhydrous ethanol.
  • 76
  • [ 4426-83-9 ]
  • [ 5818-06-4 ]
  • 4-heptyl-1-(3-hydroxybenzoyl)thiosemicarbazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% at 110℃; for 0.0833333h; 4.1.1. Synthesis of the compounds 1-22 General procedure: Equimolar amounts of various alkyl isothiocyanates and carboxylicacid hydrazides (obtained from the respective carboxylic acids) weremixed together and heated to 110 °C until a product was formed (i.e.,for 5 min). The obtained thiosemicarbazide derivatives were washedwith diethyl ether, filtered and crystallized from anhydrous ethanol.These compounds were subsequently dissolved in 2% NaOH and heatedunder reflux for 2 h. After cooling to room temperature, the solvent wasneutralized with 3M HCl to form a solid of appropriate 4-alkyl-5-substituted-1,2,4-triazole-3-thione derivative, which was filtered, dried and crystallized from anhydrous ethanol.
  • 77
  • oxovanadium(IV) sulfate [ No CAS ]
  • [ 4940-11-8 ]
  • [ 1829-34-1 ]
  • [ 5818-06-4 ]
  • C21H16BrN2O7V [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% 3-Bromosalicylaldehyde (0.200 g, 1 mmol) and 3-hydroxylbenzohydrazide (0.150 g,1 mmol) were stirred in methanol (30 mL) for 30 min. Then, ethyl maltol (0.140 g,1 mmol) and VOSO4 (0.163 g, 1 mmol) dissolved in methanol (30 mL) were added to the above solution. The mixture was further stirred for 30 min to give a deep brown solution. Single crystals were obtained by slow evaporation of the solution in air.Yield: 65%. IR data (cm-1): 3449 (OH), 1601 (CN), 949 (VO). UV-Vis data (MeOH, lambdamax, nm): 273, 325, 401. Anal. calc. for C21H16BrN2O7V: C, 46.8; H, 3.0; N, 5.2. Found: C,46.6; H, 3.1; N, 5.3%. 1H NMR (300 MHz, DMSO-d6) delta 9.72 (s, 1 H, OH), 9.24 (s, 1 H,CHN), 8.51 (d, 1 H, L'H), 7.88 (m, 2 H, ArH), 7.28 (m, 3 H, ArH), 7.02 (d, 1 H, ArH), 6.95(m, 1 H, ArH), 6.74 (d, 1 H, L'H), 3.03 (q, 2 H, CH2), 1.35 (t, 3 H, CH3).
  • 78
  • [ 75-15-0 ]
  • [ 5818-06-4 ]
  • C8H7N2O2S2(1-)*K(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide In ethanol; water Reflux; Synthesis of 5-aryl-1,3,4-oxadiazole-2-thiol derivatives (5) General procedure: Acid hydrazid (1 mmol) in EtOH (10 ml) was added to aflask containing KOH (1 mmol, dissolved in at least water),after dissolving occurred, CS2 (1.5 mmol) was addeddropwise. The reaction mixture was stirred and heated toreflux for 4-5 h, until most of the hydrogen sulfide evolved.Completion of the reaction was monitored by TLC until thestarting materials were not detected.
  • 79
  • [ 22047-25-2 ]
  • [ 5818-06-4 ]
  • (E)-3-hydroxy-N′-(1-(pyrazin-2-yl)ethylidene)benzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% In ethanol at 65℃; for 4h; (E)-3-hydroxy-N′-(1-(pyrazin-2-yl)ethylidene)benzohydrazide (HL2): A solution of 2-acetylpyrazine (1.22g, 10mmol) in ethanol (20mL) was slowly added to a solution of 3-hydroxybenzohydrazide (1.52g, 10mmol) in ethanol (20mL). The mixture solution was then refluxed at 65°C for 4h; after that, it was cooled down, suction filtered, and then washed with cold ethanol. The final product (1.65g, 64% yield) was obtained by air-drying. MS, NMR, IR, and UV data are shown in the Supporting information (Section S1).
  • 80
  • [ 41715-31-5 ]
  • [ 5818-06-4 ]
  • 3-hydroxy-N’-[(E)-(3-tert-butyl-2-hydroxy-5-methylphenyl)methylidene]benzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With acetic acid In methanol for 2h; Reflux; General procedure for the Synthesis of Hydrazide-Hydrazones 1a-j, 2a-h, 3a-g General procedure: To a mixture of aldehyde 5-7 (2.0 mmol), and carboxylic acid hydrazide 4a-c (2.0 mmol) in dryCH3OH (5.0 mL), AcOH (0-200 μL) was added at room temperature (RT) and then the resultingmixture was gently refluxed under stirring. The reaction progress was monitored by TLC. When the reaction was finished, after slow cooling to RT and further cooling to ca. 4 °C, the reaction mixturewas left overnight in a refrigerator (-24 °C). The crystals formed were collected by filtration to givepure products 1-3 which were identified by comparison of their melting points and FT-IR and/or NMRspectra with literature data and/or by HRMS measurements. The new compounds 1b, 1d, 2a-b, 2e-f,2h, and 3a-g, were fully characterized.
  • 81
  • rhoodamine 6G [ No CAS ]
  • [ 5818-06-4 ]
  • N-(3′,6′-bis(ethylamino)-2′,7′-dimethyl-3-oxospiro[isoindoline-1,9′-xanthene]-2-yl)-3-hydroxybenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 0 - 30℃; Inert atmosphere; 2.1.1.3. General procedure for the synthesis of N-(3′,6′-bis(ethyl amino)-2′,7′-dimethyl-3-oxospiro[isoindoline-1,9′-xanthene]-2-yl) (2/3/4-un/substituted-benzamides) compounds (5a-5g). General procedure: As shown in Scheme 2, rhodamine 6G (1.0 mmol) and compound (3a-3g) (1.0 mmol) were taken in DMF (8 mL) and cooled to 0-5 °C. Potassium tert-butoxide was added slowly and the reaction was stirred at 0-5 °C for 1 h thent he temperature was gradually augmented to 25-30 °C and stirred until the reaction gets completed (6-7 h/monitored by TLC) [50b]. The reaction mixture was quenched by gradual addition of the ice-cold water, the solid gets suspended in the reaction mass which was finally filtered and dried. The impure solid was purified by column chromatography, using dichloromethane/methanol (9.5:0.5) as an eluent to afford a pink coloured target compound with 80-86% yield (5a-5g).
  • 82
  • [ 75-15-0 ]
  • [ 5818-06-4 ]
  • 3-(5-mercapto-1,3,4-oxadiazol-2-yl)phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With N,N-dimethyl-formamide for 24h; Sonication; Green chemistry;
  • 83
  • [ 22532-62-3 ]
  • [ 5818-06-4 ]
  • N’-(4-bromo-2-hydroxybenzylidene)-3-hydroxybenzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol Reflux; 2. 2. Synthesis of the Complex[VOLa(emt)]·DMF General procedure: 3-Hydroxybenzohydrazide (10 mmol, 1.52 g) and4-bromosalicylaldehyde (10 mmol, 2.01 g) were refluxedin methanol (50 mL). Then, VO(acac)2 (10 mmol, 2.63 g)and ethyl maltol (10 mmol, 1.40 g) dissolved in methanol(30 mL) were added to the mixture and refluxed for 1 h inoil bath to give a deep brown solution with some insolublesubstance. Then, a few drops of DMF were added until theinsoluble substance dissolved. Single crystals of the complexwere formed during slow evaporation of the reactionmixture in air. The crystals were isolated by filtration,washed with cold methanol and dried over anhydrousCaCl2. Yield: 0.38 g (61%). IR data (KBr pellet, cm-1): 1667ν(C=O), 1592 ν(C=N), 1524, 1455, 1408, 1353, 1250ν(C-Ophenolate), 1188 ν(N-N), 1107, 1066, 1030, 973ν(V=O), 926, 850, 796, 727, 630, 522, 468. UV-Vis data inmethanol (nm): 210, 269, 320, 398. Molar conductance(10-3 mol L-1, methanol): 25 Ω-1 cm2 mol-1. Analysis:Found: C 46.89, H 3.85, N 6.77%. Calculated forC24H23BrN3O8V: C 47.08, H 3.79, N 6.86%.
  • 84
  • [ 652-36-8 ]
  • [ 5818-06-4 ]
  • 3,3'-[(2,3,5,6-tetrafluorobenzene-1,4-diyl)bis-(1,3,4-oxadiazole-5,2-diyl)]diphenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With trichlorophosphate Reflux; 1,4-Bis(5-aryl-1,3,4-oxadiazole-2-yl)-2,3,5,6-tetrafluorobenzenes 3a-3l (general procedure). General procedure: A mixture of hydrazide 1a-1l (2 mmol) and 2,3,5,6-tetrafluoroterephthalic acid (2) (1 mmol) in 5 mL of phosphoryl chloride was refluxed in a 25-mL round-bottom flask until the reaction was complete (TLC). The mixture was cooled to room temperature, poured into 50 mL of ice water with stirring, and neutralized. The solid product was filtered off, washed with water, and recrystallized from ethanol.
  • 85
  • [ 3779-27-9 ]
  • [ 5818-06-4 ]
  • N'-([2,2'-bithiophen]-5-ylmethylene)-3-hydroxybenzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
97.6% In ethanol at 60℃; for 4h; 2.2.2 (Z)-N′-([2,2′-bithiophen]-5-ylmethylene)-3-hydroxybenzohydrazide (HL2) A solution of 3-hydroxybenzohydrazide (1.52 g, 10 mmol) in ethanol (20 mL) was slowly added to a solution of [2,2′-bithiophene]-5-carbaldehyde (1.94 g, 10 mmol) in ethanol (20 mL). The mixture solution was then refluxed at 60°C for 4 h; after that, it was cooled down, filtered, and then washed with cold ethanol. The final product (3.2 g, 97.6% yield) was obtained by air-drying. MS m/z=328 (M-1). (Fig. A.2) C16H12N2O2S2: calculated: C 58.52; H 3.68; N 8.53%; found: C 58.61; H 3.64; N 8.59%. 1H NMR and DQF-COSY NMR (DMSO-d6, 600 MHz) (Fig. A.5): δ (ppm) 6.96 (s, 1H, hydroxyphenyl), 7.14 (t, 1H, thienyl, J=12Hz), 7.27 (s, 1H, thienyl), 7.32 (m, 3H, hydroxyphenyl and thienyl), 7.44 (d, 2H, hydroxyphenyl and thienyl, J=18Hz), 7.59 (d, 1H, thienyl, J=6Hz), 8.60 (s, 1H, -N=CH-), 9.76 (s, 1H, -OH), 11.77 (s, 1H, -NH-). IR (KBr): ν=3312m, 1643s, 1589s, 1540s, 1506 w, 1499 w, 1457m, 1293m, 1246 w, 1234 w, 1128 w, 1080 w, 1045 w, 997 w, 941 w, 881 w, 835m, 795 w, 735 w, 701m, 679 w, 669 w, 419 w, cm-1. UV [nm (ε, L·mol-1cm-1)] in DMSO: 373 (5.03×104).
  • 86
  • [ 134670-30-7 ]
  • [ 5818-06-4 ]
  • N'-((6-(4-fluorophenyl)imidazo[2,1-b]thiazol-5-yl)methylene)-3-hydroxybenzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With acetic acid In ethanol Reflux;
  • 87
  • [ 82588-41-8 ]
  • [ 5818-06-4 ]
  • N'-((6-(4-chlorophenyl)imidazo[2,1-b]thiazol-5-yl)methylene)-3-hydroxybenzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With acetic acid In ethanol Reflux;
  • 88
  • [ 5818-06-4 ]
  • [ 74630-73-2 ]
  • 3-hydroxy-N'-((6-phenylimidazo[2,1-b]thiazol-5-yl)methylene)benzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With acetic acid In ethanol Reflux;
  • 89
  • [ 5818-06-4 ]
  • 6-(4-methoxyphenyl)imidazo[2,1-b]thiazole-5-carbaldehyde [ No CAS ]
  • 3-hydroxy-N'-((6-(4-methoxyphenyl)imidazo[2,1-b]thiazol-5-yl)methylene)benzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With acetic acid In ethanol Reflux;
  • 90
  • C23H18N2O2 [ No CAS ]
  • [ 5818-06-4 ]
  • (E)-N'-((3-([1,1'-biphenyl]-4-yl)-1-(4-methoxyphenyl)-1H-pyrazol-4-yl)methylene)-3-hydroxybenzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid In ethanol at 75℃; for 4h;
  • 91
  • C22H15FN2O [ No CAS ]
  • [ 5818-06-4 ]
  • (E)-N'-((3-([1,1'-biphenyl]-4-yl)-1-(4-fluorophenyl)-1H-pyrazol-4-yl)methylene)-3-hydroxybenzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid In ethanol at 75℃; for 4h;
  • 92
  • [ 108446-64-6 ]
  • [ 5818-06-4 ]
  • (E)-N'-((3-([1,1'-biphenyl]-4-yl)-1-phenyl-1H-pyrazol-4-yl)methylene)-3-hydroxybenzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid In ethanol at 75℃; for 4h;
Same Skeleton Products
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