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[ CAS No. 4720-72-3 ] {[proInfo.proName]}

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Product Details of [ 4720-72-3 ]

CAS No. :4720-72-3 MDL No. :MFCD03426246
Formula : C8H8N2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 180.16 Pubchem ID :-
Synonyms :

Safety of [ 4720-72-3 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 4720-72-3 ]

* 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 [ 4720-72-3 ]

[ 4720-72-3 ] Synthesis Path-Downstream   1~53

  • 1
  • [ 4421-09-4 ]
  • [ 4720-72-3 ]
YieldReaction ConditionsOperation in experiment
94% With hydroxylamine hydrochloride; N-ethyl-N,N-diisopropylamine In ethanol at 20℃; for 21.5h; 1.6 DIPEA (12.17 ml, 69.7 mmol) was added to a suspension of piperonylonitrile (5 g, 34.0 mmol) and hydroxylamine hydrochloride (4.72 g, 68.0 mmol) in EtOH (75 mL). After stirring at 20° C. for 21.5 h, the reaction mixture was concentrated to dryness. The resulting colorless oil was cooled to 0° C. and cold water was added (75.0 mL) and the mixture was stirred for 30 minutes to give a white slurry. The solids were filtered, washed with water (2×15 mL) and the resulting solid dried at 40° C. under high vacuum until constant weight to afford Intermediate 6a (Z)-N′-hydroxybenzo[d][1,3]dioxole-5-carboximidamide (5.76 g, 94% yield) as a white solid: 1H NMR (DMSO-d6) is consistent with the desired product; MS m/z 181.1 (MH+); HPLC 100%, Rt=0.16 (0.31) min. Alternatively DIPEA can be replaced by sodium carbonate or commercial sodium ethoxide while working in ethanol as solvent for the reaction. Except when commercially available, all N′-hydroxycarboximidamides cited in the examples hereafter were prepared following the recipe outline before for intermediate 6a with the appropriate nitrile precursor and including its variation on the nature of the base used.
73.5% With hydroxylamine hydrochloride; sodium carbonate In ethanol at 80℃; for 5h; Description 2: (Z)-N' -hydroxybenzo[d][l,3]dioxole-5-carboximidamide Description 2: (Z)-N' -hydroxybenzo[d][l,3]dioxole-5-carboximidamide To a solution of benzo[d][l,3]dioxole-5-carbonitrile (15 g, 102 mmol), hydroxylamine hydrochloride (14.17 g, 204 mmol) in Ethanol (500 mL) was added Na2C03 (54.0 g, 510 mmol) in one charge. The reaction mixture was stirred at 80°C for 5 hr. Then the solvent was removed under reduced pressure, the residual was washed with DCM (1L><4), filtered and the combined filtrate was concentrated under reduced pressure to afford (Z)-N'-hydroxy benzo[d][l,3]dioxole-5-carboximidamide as a yellow solid (15 g, 73.5%). MS(ES+) m/z 181.1 (MH+).
73.5% With hydroxylamine hydrochloride; sodium carbonate In ethanol at 80℃; for 5h; 2 Description 2: (Z)-N'-hydroxybenzo[d][1,3]dioxole-5-car boximidamide To a solution of benzo[d][1,3]dioxole-5-carbonitrile (15 g, 102 mmol), hydroxylamine hydrochloride (14.17 g, 204 mmol) in Ethanol (500 mL) was added Na2CO3 (54.0 g, 510 mmol) in one charge. The reaction mixture was stirred at 80° C. for 5 hr. Then the solvent was removed under reduced pressure, the residual was washed with DCM (1 L×4), filtered and the combined filtrate was concentrated under reduced pressure to afford (Z)-N′-hydroxy benzo[d][1,3]dioxole-5-carboximidamide as a yellow solid (15 g, 73.5%). MS (ES+) m/z 181.1 (MH+).
With ethanol; hydroxylamine at 60℃;
With ethanol; hydroxylamine hydrochloride; water; sodium carbonate
With hydroxylamine at 110℃; im Rohr;
With hydroxylamine hydrochloride; triethylamine In ethanol at 80℃; for 4h; Inert atmosphere; Schlenk technique;
With hydroxylamine hydrochloride; triethylamine In ethanol at 80℃; for 4h; Inert atmosphere; Schlenk technique;
With hydroxylamine hydrochloride; triethylamine In water at 20℃; for 6h;

  • 2
  • [ 4720-72-3 ]
  • [ 717110-11-7 ]
  • (3R,4S)-4-(4-Chloro-phenyl)-1-methyl-piperidine-3-carboxylic acid {benzo[1,3]dioxol-5-yl-[(Z)-hydroxyimino]-methyl}-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine In chloroform Heating;
  • 3
  • [ 4720-72-3 ]
  • [ 696660-34-1 ]
  • (3S,4R)-4-(4-Chloro-phenyl)-1-methyl-piperidine-3-carboxylic acid {benzo[1,3]dioxol-5-yl-[(Z)-hydroxyimino]-methyl}-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine In chloroform Heating;
  • 4
  • [ 4720-72-3 ]
  • [ 717111-93-8 ]
  • (3R,4S)-3-(3-Benzo[1,3]dioxol-5-yl-[1,2,4]oxadiazol-5-ylmethyl)-4-(4-chloro-phenyl)-1-methyl-piperidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
65 mg Stage #1: N′-hydroxybenzo[d][1,3]dioxole-5-carboximidamide; [(3R,4S)-4-(4-Chloro-phenyl)-1-methyl-piperidin-3-yl]-acetyl chloride With pyridine Heating; Stage #2: With acetic acid Heating;
  • 6
  • [ 4421-09-4 ]
  • [ 4720-72-3 ]
YieldReaction ConditionsOperation in experiment
100% With hydroxylamine In ethanol; water at 80℃; for 5h; 4.1.2. General Procedure for the Automated Synthesis of Compounds 6 and 7 General procedure: Nitrile (20.00 mmol), ethanol (30.0 mL) and hydroxylamine (50% in water, 2.0 mL) were addedin a 75 mL double jacket reactor from Chemspeed equipped with condenser. The mixture was shakenat 600 rpm for 5 h at 80 °C, then cooled down to 20 °C. The reaction medium was evaporated underreduced pressure and the solid was finally dried overnight in a heated (40 °C) vacuum oven. 3,4-(Methylenedioxy)benzamidoxime (6): White solid, yield: quant. 1H-NMR (300MHz, DMSO) δ ppm:9.51 (s, 1H), 7.22-7.16 (m, 2H), 6.93-6.88 (m, 1H), 6.03 (s, 2H), 5.72 (s, 2H). 13C-NMR (125.75 MHz,DMSO) δ ppm: 150.98, 148.25, 147.56, 127.87, 119.75, 108.30, 106.17, 101.61.
89% With hydroxylamine hydrochloride; triethylamine In ethanol at 20℃; for 48h; Inert atmosphere;
80% With hydroxylamine; sodium hydrogencarbonate In ethanol; water for 3h; Reflux;
78% With hydroxylamine hydrochloride; sodium hydrogencarbonate In ethanol for 6h; Reflux; Preparation of amidoximes 1a-o. General procedure [1]. General procedure: To a stirred suspension of corresponding nitrile and hydroxylamine hydrochloride (1.5 equiv.) in EtOH (10 mL per gram of nitrile) a NaHCO3 (1.5 equiv.) was added. The reaction mixture was stirred under reflux for a 6 h. After the reaction had completed, the reaction mixture was concentrated under reduced pressure, and the residue was diluted with cold water (200 mL). The resulting precipitate was filtered off and washed with cold water (50 mL).
65% With hydroxylamine hydrochloride; sodium carbonate In methanol; water at 120℃; for 12h; Schlenk technique; Inert atmosphere;
64% With hydroxylamine hydrochloride; triethylamine In water at 25℃; for 6h; Green chemistry; General procedure for the synthesis of arylamidoximes 2a-g General procedure: A mixture of aryl nitrile 1a-g (20 mmol), hydroxylamine hydrochloride (2.08 g, 30 mmol) and triethylamine (4.46 mL, 32 mmol) in 40 mL distilled water was stirred at room temperature (25 °C) for 6 h. After completion of the reaction (monitored by TLC), the products of 2b-g were filtered, washed with distilled water, dried and used without further purification. But in the case of benzamidoxime 2a, it was extracted from the reaction mixture using ethyl acetate (3 * 30 mL), the organic layer was then dried over anhydrous MgSO4, filtered and evaporated by using a rotary evaporator. The residue was purified by silica gel column chromatography using petroleum ether/ethyl acetate (6 :1) as eluent.
With hydroxylamine hydrochloride; sodium hydrogencarbonate In ethanol; water for 12h; Reflux;
With hydroxylamine hydrochloride; triethylamine In ethanol at 78℃;
With hydroxylamine In ethanol; water for 3h; Reflux; Inert atmosphere;
With hydroxylamine hydrochloride In ethanol at 100℃; Inert atmosphere;
With hydroxylamine hydrochloride; sodium carbonate In ethanol at 80℃;
With hydroxylamine In ethanol; water for 3h; Reflux;
With hydroxylamine hydrochloride; sodium carbonate In ethanol; water at 20℃;
With hydroxylamine In acetonitrile for 3h; Reflux;
With hydroxylamine hydrochloride; sodium hydrogencarbonate In ethanol; water at 20℃;
With hydroxylamine hydrochloride; triethylamine In ethanol at 60℃; 2.1. General procedure for the synthesis of amidoximes 1a-1r General procedure: A mixture of benzonitrile (10 g, 97.0 mmol, 1.0 equiv.), hydroxylamine hydrochloride (145.5 mmol, 1.5 equiv.), triethylamine (145.5 mmol, 1.5 equiv.) in ethanol (100 ml) was stirred in a 250ml three-necked round-bottom flask at 60 °C for 6 hours. Reaction was monitored by TLC. When the reaction reached completion, reaction mixture was concentrated in vacuum with silica gel added. The residue was put on flash chromatography column (petroleum ether/ethyl acetate) to isolate the amidoxime 1, further purified via recrystallization.
With hydroxylamine hydrochloride; potassium carbonate In methanol Reflux;

Reference: [1]Stevanovic, Strahinja; Sencanski, Milan; Danel, Mathieu; Menendez, Christophe; Belguedj, Roumaissa; Bouraiou, Abdelmalek; Nikolic, Katarina; Cojean, Sandrine; Loiseau, Philippe M.; Glisic, Sanja; Baltas, Michel; García-Sosa, Alfonso T. [Molecules, 2019, vol. 24, # 7]
[2]Keurulainen, Leena; Heiskari, Mikko; Nenonen, Satu; Nasereddin, Abedelmajeed; Kopelyanskiy, Dmitry; Leino, Teppo O.; Yli-Kauhaluoma, Jari; Jaffe, Charles L.; Kiuru, Paula [MedChemComm, 2015, vol. 6, # 9, p. 1673 - 1678]
[3]Koryakova, Angela G.; Ivanenkov, Yan A.; Ryzhova, Elena A.; Bulanova, Elena A.; Karapetian, Ruben N.; Mikitas, Olga V.; Katrukha, Eugeny A.; Kazey, Vasily I.; Okun, Ilya; Kravchenko, Dmitry V.; Lavrovsky, Yan V.; Korzinov, Oleg M.; Ivachtchenko, Alexandre V. [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 12, p. 3661 - 3666]
[4]Presnukhina, Sofia; Tarasenko, Marina; Baykov, Sergey; Smirnov, Sergey N.; Boyarskiy, Vadim P.; Shetnev, Anton; Korsakov, Mikhail K. [Tetrahedron Letters, 2020, vol. 61, # 9]
[5]Yang, Chu-Ting; Han, Jun; Liu, Jun; Gu, Mei; Li, Yi; Wen, Jun; Yu, Hai-Zhu; Hu, Sheng; Wang, Xiaolin [Organic and Biomolecular Chemistry, 2015, vol. 13, # 9, p. 2541 - 2545]
[6]Albayati, Mustafa R.; Mohamed, Mamdouh F. A.; Moustafa, Amr H. [Synthetic Communications, 2020, vol. 50, # 8, p. 1217 - 1231]
[7]Location in patent: experimental part Konyushkin; Godovikova; Vorontsova; Tsyganov; Karmanova; Raihstat; Firgang; Pokrovskii; Pokrovskii; Semenova; Semenov [Russian Chemical Bulletin, 2010, vol. 59, # 12, p. 2268 - 2275]
[8]Zora, Metin; Kivrak, Arif; Kelgokmen, Yilmaz [Journal of Organometallic Chemistry, 2014, vol. 759, p. 67 - 73]
[9]Yang, Fan; Yu, Jiaojiao; Liu, Yun; Zhu, Jin [Organic Letters, 2017, vol. 19, # 11, p. 2885 - 2888]
[10]Shi, Wei-Min; Li, Xiao-Hua; Liang, Cui; Mo, Dong-Liang [Advanced Synthesis and Catalysis, 2017, vol. 359, # 23, p. 4129 - 4135]
[11]Zhang, Jing; Sun, Jun-Shu; Xia, Ying-Qi; Dong, Lin [Advanced Synthesis and Catalysis, 2019, vol. 361, # 9, p. 2037 - 2041]
[12]Zhang, Guofu; Zhao, Yiyong; Ding, Chengrong [Organic and Biomolecular Chemistry, 2019, vol. 17, # 33, p. 7684 - 7688]
[13]Guido, Rafael V. C.; Leal, Laylla L. L.; Maciel, Larissa G.; Oliveira, Andrew A.; Romão, Tatiany P.; Silva-Filha, Maria Helena N. L.; Soares, Thereza A.; dos Anjos, Janaína V. [Bioorganic and medicinal chemistry, 2020, vol. 28, # 2]
[14]Ding, Chengrong; Ge, Shuting; Wei, Junjie; Zhang, Guofu; Zhao, Yiyong [RSC Advances, 2020, vol. 10, # 29, p. 17288 - 17292]
[15]Barbosa, Andrey da S.; Barbosa, Andrey da S.; Maciel, Larissa G.; Soares, Thereza A.; de Alencar-Filho, Edilson B.; dos Anjos, Janaína V.
[16]Wang, Xuetong; Wang, Yin; Liu, Xiaoling; He, Tingshu; Li, Lingli; Wu, Huili; Zhou, Shangjun; Li, Dan; Liao, Siwei; Xu, Ping; Huang, Xing; Yuan, Jianyong [Tetrahedron, 2021, vol. 100]
[17]Mohamed, Mamdouh F.A.; Marzouk, Adel A.; Nafady, Ayman; El-Gamal, Dalia A.; Allam, Rasha M.; Abuo-Rahma, Gamal El-Din A.; El Subbagh, Hussein I.; Moustafa, Amr H. [Bioorganic Chemistry]
  • 7
  • [ 55-22-1 ]
  • [ 4720-72-3 ]
  • [ 892422-01-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: N′-hydroxybenzo[d][1,3]dioxole-5-carboximidamide With 1,1'-carbonyldiimidazole In acetonitrile at 20℃; for 1h; Stage #2: pyridine-4-carboxylic acid In acetonitrile at 20℃; for 12h;
  • 8
  • [ 98-97-5 ]
  • [ 4720-72-3 ]
  • C13H10N4O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: N′-hydroxybenzo[d][1,3]dioxole-5-carboximidamide With 1,1'-carbonyldiimidazole In acetonitrile at 20℃; for 1h; Stage #2: 2-pyrazylcarboxylic acid In acetonitrile at 20℃; for 12h;
  • 9
  • [ 498-94-2 ]
  • [ 4720-72-3 ]
  • C14H17N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: N′-hydroxybenzo[d][1,3]dioxole-5-carboximidamide With 1,1'-carbonyldiimidazole In acetonitrile at 20℃; for 1h; Stage #2: isonipecotic acid In acetonitrile at 20℃; for 12h;
  • 10
  • [ 94-53-1 ]
  • [ 4720-72-3 ]
  • [ 888178-53-8 ]
YieldReaction ConditionsOperation in experiment
Stage #1: N′-hydroxybenzo[d][1,3]dioxole-5-carboximidamide With 1,1'-carbonyldiimidazole In acetonitrile at 20℃; for 1h; Stage #2: Piperonylic acid In acetonitrile at 20℃; for 12h;
  • 11
  • [ 134-11-2 ]
  • [ 4720-72-3 ]
  • [ 892433-52-2 ]
  • 12
  • [ 586-38-9 ]
  • [ 4720-72-3 ]
  • [ 888167-35-9 ]
YieldReaction ConditionsOperation in experiment
Stage #1: N′-hydroxybenzo[d][1,3]dioxole-5-carboximidamide With 1,1'-carbonyldiimidazole In acetonitrile at 20℃; for 1h; Stage #2: 3-Methoxybenzoic acid In acetonitrile at 20℃; for 12h;
  • 13
  • [ 93-07-2 ]
  • [ 4720-72-3 ]
  • [ 892444-37-0 ]
YieldReaction ConditionsOperation in experiment
Stage #1: N′-hydroxybenzo[d][1,3]dioxole-5-carboximidamide With 1,1'-carbonyldiimidazole In acetonitrile at 20℃; for 1h; Stage #2: Veratric acid In acetonitrile at 20℃; for 12h;
  • 14
  • [ 4720-72-3 ]
  • [ 1221719-41-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 1,1'-carbonyldiimidazole / acetonitrile / 1 h / 20 °C 1.2: 12 h / 20 °C 2.1: N,N-dimethyl-formamide / 3 h / 120 - 125 °C
  • 15
  • [ 4720-72-3 ]
  • [ 849925-04-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 1,1'-carbonyldiimidazole / acetonitrile / 1 h / 20 °C 1.2: 12 h / 20 °C 2.1: N,N-dimethyl-formamide / 3 h / 120 - 125 °C
  • 16
  • [ 4720-72-3 ]
  • [ 889960-26-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 1,1'-carbonyldiimidazole / acetonitrile / 1 h / 20 °C 1.2: 12 h / 20 °C 2.1: N,N-dimethyl-formamide / 3 h / 120 - 125 °C
  • 17
  • [ 4720-72-3 ]
  • [ 889955-42-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 1,1'-carbonyldiimidazole / acetonitrile / 1 h / 20 °C 1.2: 12 h / 20 °C 2.1: N,N-dimethyl-formamide / 3 h / 120 - 125 °C
  • 18
  • [ 4720-72-3 ]
  • [ 884979-32-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 1,1'-carbonyldiimidazole / acetonitrile / 1 h / 20 °C 1.2: 12 h / 20 °C 2.1: N,N-dimethyl-formamide / 3 h / 120 - 125 °C
  • 19
  • [ 4720-72-3 ]
  • [ 885002-83-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 1,1'-carbonyldiimidazole / acetonitrile / 1 h / 20 °C 1.2: 12 h / 20 °C 2.1: N,N-dimethyl-formamide / 3 h / 120 - 125 °C
  • 20
  • [ 4720-72-3 ]
  • [ 885002-32-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 1,1'-carbonyldiimidazole / acetonitrile / 1 h / 20 °C 1.2: 12 h / 20 °C 2.1: N,N-dimethyl-formamide / 3 h / 120 - 125 °C
  • 21
  • [ 4720-72-3 ]
  • [ 118-41-2 ]
  • [ 765269-67-8 ]
YieldReaction ConditionsOperation in experiment
Stage #1: N′-hydroxybenzo[d][1,3]dioxole-5-carboximidamide With 1,1'-carbonyldiimidazole In acetonitrile at 20℃; for 1h; Stage #2: Eudesmic acid In acetonitrile at 20℃; for 12h;
  • 22
  • [ 4720-72-3 ]
  • [ 99-96-7 ]
  • C15H12N2O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: N′-hydroxybenzo[d][1,3]dioxole-5-carboximidamide With 1,1'-carbonyldiimidazole In acetonitrile at 20℃; for 1h; Stage #2: 4-hydroxy-benzoic acid In acetonitrile at 20℃; for 12h;
  • 23
  • [ 108-55-4 ]
  • [ 4720-72-3 ]
  • 4-[3-(benzo[d][1,3]dioxol-5-yl)-1,2,4-oxadiazol-5-yl]butanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% In neat (no solvent) at 130℃; 4 Synthesis of 3-(3-aryl-1,2,4-oxadiazol-5-yl)-butanoic acids (5a-g) General procedure: A suitable arylamidoxime 3a-g (1.0mmol) was allowed to react with glutaric anhydride 4 (1.2mmol) in a round bottom flask, with no solvent, at 130°C (oil bath) for 3-4h. When TLC analysis indicated the complete consumption of the starting amidoxime, the reaction was cooled to room temperature, The reaction mixture was then diluted with a concentrated solution of NaHCO3 (10mL) and AcOEt (10mL) and this resulting suspension was allowed to stir overnight. The aqueous layer was separated and then a concentrated solution of citric acid was added until total precipitation of the desired compounds. The obtained product was dissolved in chloroform, dried over anhydrous Na2SO4 and re-crystallized from chloroform-hexane to afford the pure products (5a-g). 4.1.1 .4 4-[3-(Benzo[d][1,3]dioxol-5-yl)-1,2,4-oxadiazol-5-yl]butanoic acid (5g) Yield: 60%, mp (°C): 112-113. 1H NMR (400 MHz, CDCl3) δ (ppm): 2.21 (q, J = 7.6 Hz, 6.8 Hz, 2H); 2.56 (t, J = 7.6 Hz, 2H); 3.03 (t, J = 6.8 Hz, 2H); 6.03 (s, 2H); 6.89 (dd; J = 8.4 Hz, 1.6 Hz, 1H); 7.51 (d, J = 1.6 Hz, 1H); 7.63 (dd, J = 8.4 Hz, 1H). C NMR (100 MHz, CDCl3) δ (ppm): 21.4, 25.6, 32.6, 101.6, 107.5, 108.6, 120.6, 122.3, 148.1, 150.1, 167.9, 177.8, 178.7. Elemental analysis for C13H12N2O5: Calcd C, 56.52; H, 4.38; N, 10.14. Found C, 56.70; H, 4.08; N, 9.82.
In neat (no solvent) at 140℃;
  • 24
  • 3-(ferrocenyl)propiolaldehyde [ No CAS ]
  • [ 4720-72-3 ]
  • [ 1608090-98-7 ]
YieldReaction ConditionsOperation in experiment
82% With potassium hydroxide In 1,4-dioxane at 100℃; Inert atmosphere; General procedure for the one-pot synthesis of 5-ferrocenyl-1,2,4-oxadiazoles (10) in the presence of KOH (Table1) General procedure: To a stirred solution of 3-ferrocenylpropynal (6) (0.25 mmol) in dioxane (7.5 mL) under argon was added the proper amidoxime 2 (0.32 mmol) and KOH (0.25 mmol) and the resulting mixture was heated under reflux for appropriate time. The progress of the reaction was monitored by routine TLC for the disappearance of 3-ferrocenylpropynal (6). After the reaction was over, the mixture was allowed to cool to room temperature and filtrated to remove undissolved KOH. Organic solvent was then removed on a rotary evaporator to give the crude product, which was purified by flash column chromatography on silica gel using hexane/ethyl acetate (9:1) as the eluent to afford the corresponding 5-ferrocenyl-1,2,4-oxadiazole derivative 10.
  • 25
  • [ 2635-13-4 ]
  • [ 4720-72-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium diacetate; 1,1'-bis-(diphenylphosphino)ferrocene; sodium carbonate; 1-methyl-pyrrolidin-2-one / 12 h / 120 °C / Schlenk technique; Inert atmosphere 2: sodium carbonate; hydroxylamine hydrochloride / methanol; water / 12 h / 120 °C / Schlenk technique; Inert atmosphere
  • 26
  • [ 4720-72-3 ]
  • [ 938-18-1 ]
  • (Z)-N'-((2,4,6-trimethylbenzoyl)oxy)benzo[d][1,3]dioxole-5-carboximidamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With triethylamine In tetrahydrofuran at 20℃; for 4h; 26 To a solution of 2,4,6-trimethylbenzoyl chloride (obtained as described in Intermediate 5a) in THF (2.5 mL) and (Z)-N'-hydroxybenzo[d][1,3]dioxole-5-carboximidamide (90 mg, 0.499 mmol) was added triethylamine (0.139 mL, 0.999 mmol). After stirring at room temperature for 4 h and following the standard isolation procedure gave a crude product which treated briefly in a mixture of DCM:Et2O:pentane to afford 124 mg (76%) of (Z)-N'-((2,4,6-rimethylbenzoyl)oxy)benzo[d][1,3]dioxole-5-carboximidamide as a white solid: 1H NMR (400 MHz, DMSO-d6)_ppm 2.25 (s, 6H) 2.26 (s, 3H) 6.09 (s, 2H) 6.68 (br. s., 2H) 6.93 (s, 2H) 6.98 (d, J=8.22 Hz, 1H) 7.24 (d, J=1.57 Hz, 1H) 7.29 (dd, J=8.22, 1.96 Hz, 1H); MS m/z 327.1399 (MH+); HPLC >99.5%, column 2.
  • 27
  • [ 103-71-9 ]
  • [ 4720-72-3 ]
  • N'-[(phenylcarbamoyl)oxy]benzo[d][1,3]dioxole-5-carboximidamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
6% In chloroform at 20℃; for 72h; Inert atmosphere;
  • 28
  • [ 4720-72-3 ]
  • 8,9-bis(4-methoxyphenyl)-[1,3]dioxolo[4,5-f]isoquinolin-6-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / 24 h / 110 °C / Inert atmosphere 2: carbonyl(pentamethylcyclopentadienyl)cobalt diiodide; lithium acetate; silver hexafluoroantimonate / 2,2,2-trifluoroethanol / 12 h / 90 °C / Inert atmosphere; Sealed tube
  • 29
  • [ 75-36-5 ]
  • [ 4720-72-3 ]
  • 3-(benzo[d][1,3]dioxol-5-yl)-5-methyl-1,2,4-oxadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
4.1 g With pyridine at 110℃; for 24h; Inert atmosphere;
  • 30
  • diphenyl(trifluoromethanesulfonato)-λ3-iodane [ No CAS ]
  • [ 4720-72-3 ]
  • (Z)-N'-phenoxybenzo[d][1,3]dioxole-5-carboximidamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With 3Å molecular sieve In 1,2-dichloro-ethane at 20 - 70℃; for 15h; Schlenk technique;
  • 31
  • [ 2905-67-1 ]
  • [ 4720-72-3 ]
  • 3-(1,3-benzodioxol-5-yl)-5-(3,5-dichlorophenyl)-1,2,4-oxadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With sodium hydroxide; In dimethyl sulfoxide; at 20℃; for 2.25h; To a solution of N-hydroxy-1,3-benzodioxole-5-carboximidamide (180 mg, 1 mmol) and <strong>[2905-67-1]methyl 3,5-dichlorobenzoate</strong> (308 mg, 1 .5 mmol) in DMSO (3 mL) powdered NaOH (60 mg, 1.5 mmol) was rapidly added. The solid precipitates after 15 mm stirring. The heterogeneous mixture was stirred at room temperature for 2 h (TLC control, Si02, n-Hexane: EtOAc = 1:1,educt Rf = 0.32, product Rf = 0.91). The reaction mixture was diluted with cold water(30 mL). The resulting precipitate was filtered off, washed with water (3x10 mL) and air driedat 50 C to give the product an1e171129 as a white crystalline solid (264 mg, 788 pmol,79%).1H NMR (400 MHz, ODd3) 6 = 8.08 (d, J = 1.9 Hz, 2H), 7.73 (dd, J 8.1, 1.6 Hz, 1H), 7.59 (d,J= 1.6 Hz, 1H), 7.58 (d,J= 1.9 Hz, 1H),6.93(d,J8.1 Hz, 1H),6.06(s,2H).130 NMR (100.6 MHz, DMSO-d6) oe 173.1, 168.8, 150.4, 148.2, 136.1 (20), 132.5, 126.8,126.4(20), 122.5, 120.2, 108.7, 107.5, 101.7.LC MS (RP18-100A, gradient 50% CH3CN /50% H20 - 100% CH3CN in 30 mm), RT 27.1 mm and mass 335.04 (100%), 337.12 (65%) ([M+H]).M.p. 182-3 C.
  • 32
  • [ 618-89-3 ]
  • [ 4720-72-3 ]
  • 3-(1,3-benzodioxol-5-yl)-5-(3-bromophenyl)-1,2,4-oxadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With sodium hydroxide; In dimethyl sulfoxide; at 20℃; for 3.25h; The title compound was prepared according to the published protocol5. To a solution ofN-hydroxy-1,3..benzodioxole-5-carboximidamide (360 mg, 2 mmol) and methyl3-bromobenzoate (645 mg, 3 mmol) in DMSO (3 mL) powdered NaOH (120 mg, 3.0 mmol)was rapidly added. The solid precipitate was formed after 15 mm stirring. The heterogeneous mixture was stirred at room temperature for 3 h. The reaction mixture was diluted with cold water (60 mL). The resulting precipitate was filtered off, washed with water (3x30 mL) and air dried to provide the product sery564 as a white crystalline solid (545 mg, 79%).TLC (hexane:EtOAc, 7/1 v/v): RE = 0.55.1H NMR (400 MHz, CDCI3) 6 = 8.35 (t, J = 1.6 Hz, 1H), 8.12 (dt, J = 7.8, 1.3 Hz, 1H), 7.75-7.70 (m, 2H), 7.59(d, J= 1.7 Hz, 1H), 7.42 (t, J= 7.8 Hz, 1H), 6.93 (d, J= 8.1 Hz, 1H), 6.05(s, 2H).l3 NMR (100.6 MHz, ODd3) 6 = 174.2, 168.8, 150.4, 148.3, 135.8, 131.2, 130.8, 126.7,126.4, 123.3, 122.6, 120.6, 108.8, 107.7, 101.8.LC MS (RP18-100A, gradient 0% CH3CN/100% H20 100% CH3CN in 50 mm), RT 46.9 mm and mass 344.92 (100%), 346.95 (100%) ([M+H]).M.p. 163-164 00.
  • 33
  • [ 22204-53-1 ]
  • [ 4720-72-3 ]
  •  N'-[2-(6-methoxy-2-naphthyl)propanoyl]oxy}-1,3-benzodioxole-5-carboximidamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% Stage #1: (2S)-2-(6-methoxy(2-naphthyl))propanoic acid With 1,1'-carbonyldiimidazole In acetonitrile at 20℃; for 0.5h; Stage #2: N′-hydroxybenzo[d][1,3]dioxole-5-carboximidamide In acetonitrile for 3h; 4 4.1.1 General procedure for the synthesis of N'-[2-(6-Methoxy-2-naphthyl) propanoyl]oxy}aryl carboximidamides (3b-g) General procedure: To a solution of naproxen 1 (10 mmole, 1.2g) in 30ml acetonitrile, the N,N'-carbonyldiimidazole CDI (11 mmole, 1.2g) was added and the mixture was stirred at room temperature for 30min. The respective amidoximes 2b-g (10 mmole) was then added and stirred for further 3 hrs. After completion of reaction (monitored with TLC), the formed precipitate 3b-g was collected by filtration, washed several times with acetonitrile, dried and used without further purification.
  • 34
  • [ 22204-53-1 ]
  • [ 4720-72-3 ]
  • 5-[1-(6-methoxy-2-naphthyl)ethyl]-3-(1,3-benzodioxol-5-yl)-1,2,4-oxadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% Stage #1: (2S)-2-(6-methoxy(2-naphthyl))propanoic acid With 1,1'-carbonyldiimidazole In acetonitrile at 20℃; for 0.5h; Stage #2: N′-hydroxybenzo[d][1,3]dioxole-5-carboximidamide In acetonitrile for 27h; Reflux; 4 4.1.2 General procedure for the synthesis of 5-[1-(6-Methoxy-2-naphthyl)ethyl]-3-aryl-1,2,4-oxadiazole (4b-g) General procedure: To a solution of naproxen 1 (10 mmole, 1.2g) in 30ml acetonitrile, the N,N'-carbonyldiimidazole CDI (11 mmole, 1.2g) was added and the mixture was stirred at room temperature for 30 mins. The respective amidoximes 2b-g (10 mmole) was then added and stirred 3 hrs. After that, the reaction mixture was refluxed for 24 hrs (monitored with TLC) and cooled to room temperature. The formed precipitate 4b-g was collected by filtration, dried and recrystallized from ethanol.
  • 35
  • [ 38870-89-2 ]
  • [ 75-05-8 ]
  • [ 4720-72-3 ]
  • 3-[3,4-(methylenedioxy)phenyl]-5-(methoxymethyl)-1,2,4-oxadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With triethylamine at 130℃; for 1h; Sealed tube; Microwave irradiation; 4.1.3. Procedure for the Synthesis of Compound 8 A mixture of 3,4-(methylenedioxy)benzamidoxime (6, 180 mg, 1.00 mmol), acetonitrile (3.0 mL),thiethylamine (153 μL, 1.10 mmol) and methoxyacetyl chloride (91 μL, 1.00 mmol) was placed in asealed vial and exposed to microwave irradiation (130 °C, 1 h). The reaction medium was evaporatedunder reduced pressure and the solid was washed with 15 mL of ethyl acetate to give 8 (188 mg, 80%yield). 3-[3,4-(Methylenedioxy)phenyl)]-5-(methoxymethyl)-1,2,4-oxadiazole (8): Light tan solid, m.p.: 56-57 °C.LC purity (254 nm): 98%. 1H-NMR (300MHz, DMSO) δ ppm: 7.58 (dd, J = 8.1, 1.8 Hz, 1H), 7.45 (dd, J= 1.5, 0.3 Hz, 1H), 7.09 (dd, J = 8.1, 0.3 Hz, 1H), 6.14 (s, 2H), 4.80 (s, 2H), 3.42 (s, 3H). 13C-NMR (75MHz, DMSO) δ ppm: 176.5, 167.2, 150.1, 148.0, 122.1, 119.6, 109.0, 106.6, 101.9, 64.4, 58.8. HRMS (DCI-CH4, TOF) m/z: [M + H]+ calc. for C11H11N2O4: 235.0719. Found: 235.0712.
  • 36
  • 1-((4-fluorophenyl)ethynyl)-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one [ No CAS ]
  • [ 4720-72-3 ]
  • 3-(benzo[d][1,3]dioxol-5-yl)-6-((2-(benzo[d][1,3]dioxol-5-yl)-4-(4-fluorophenyl)-1H-imidazol-1-yl)oxy)-6-(4-fluorophenyl)-5,6-dihydro-4H-1,2,4-oxadiazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% With potassium hydroxide In tetrahydrofuran for 0.5h; Sealed tube; Reflux; chemoselective reaction;
  • 37
  • [ 4720-72-3 ]
  • [ 853658-14-7 ]
  • trans-3-(3-(benzo[d][1,3]dioxol-5-yl)-1,2,4-oxadiazol-5-yl)bicyclo[2.2.1]heptane-2-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With sodium hydroxide In dimethyl sulfoxide at 20℃; for 20h; diastereoselective reaction;
  • 38
  • [ 4720-72-3 ]
  • N-(benzo[d][1,3]dioxol-5-yl)cyanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
147.4 mg With fluorosulfonyl fluoride; triethylamine In dichloromethane at 20℃; for 2h; Schlenk technique;
With fluorosulfonyl fluoride; triethylamine In dichloromethane at 20℃; for 2h;
  • 39
  • [ 108-55-4 ]
  • [ 4720-72-3 ]
  • sodium 4-[3-(benzo[d][1,3]dioxol-5-yl)-1,2,4-oxadiazol-5-yl]butanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% Stage #1: glutaric anhydride,; N′-hydroxybenzo[d][1,3]dioxole-5-carboximidamide at 199.84℃; for 1h; Stage #2: With sodium hydroxide In methanol at 20℃; for 1h; 4.6. Synthesis of sodium 4-(3-phenyl-1,2,4-oxadiazol-5-yl)butanoate salts General procedure: In a round-bottom flask, the respective 4-(3-phenyl-1,2,4-oxadiazol-5-yl)butanoic acid (0.8 mmol) and 3.2 mL of 1% NaOH methanol solution(freshly prepared) were mixed and the reaction was allowed tostir for one hour. After the time, methanol was evaporated and theproduct was recrystallized from chloroform.
  • 40
  • [ 6118-51-0 ]
  • [ 4720-72-3 ]
  • C16H11N2O6(1-)*Na(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride; N′-hydroxybenzo[d][1,3]dioxole-5-carboximidamide In dimethyl sulfoxide at 20℃; Stage #2: With sodium hydroxide In dimethyl sulfoxide at 20℃; diastereoselective reaction; Synthesis and characterization of 1,2,4-oxadiazoles-5-yl-acrylic acids 4a-o General procedure: To a solution of amidoxime 1 (1 mmol) in dry DMSO (1 mL) exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride 2 (182 mg, 1.1 mmol) was added and the reaction mixture was stirred at room temperature for 20 h. Then powdered NaOH (92 mg, 2.3 mmol) was rapidly added. After addition, the reaction mixture was stirred at room temperature for 1 h. Then the reaction mixture was diluted with CF3COOH (0.46 mL, 6 mmol) and stirred at 60-70 °C for 1 h. After cooling to the room temperature was diluted with cold water (5 mL), the precipitate was filtered, was with cold water (2 x 2 mL) and dried in air at 50 °C. The crude compound was recristallizated from Et2O or chromatographed on silica gel using CH2Cl2/MeOH (1 : 0.05) as eluent.
  • 41
  • [ 120-57-0 ]
  • [ 4720-72-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydroxylamine / acetonitrile / 2 h / Reflux 2: triethylamine; fluorosulfonyl fluoride / acetonitrile / 0.5 h / 20 °C 3: hydroxylamine / acetonitrile / 3 h / Reflux
Stage #1: piperonal With ammonium hydroxide; iodine In acetonitrile at 20℃; for 4h; Stage #2: With hydroxylamine hydrochloride; potassium carbonate In water; isopropyl alcohol for 6h; Reflux; 4.4.8. Procedure for synthesis of compounds 29b To a solution of piperonyl aldehyde (2 mmol), iodine (558.4 mg,2.2 mmol) and 28% ammonia hydroxide solution (2 mL) in ACN (4 mL)were stirred for 4 h at room temperature. The excess iodine wasquenched by concentrated Na2S2O3 solution, and the reaction mixturewas concentrated by reduced pressure and the residue were filtratedand washed by water. Following, the residue was mixed with hydroxylaminehydrochloride (140.1 mg, 2.0 mmol), K2CO3 (138.5 mg,1 mmol) and water (1.5 mL) in isopropyl alcohol (3.5 mL) and refluxedfor 6 h. After cooling down, the resulting mixture was concentrated byreduced pressure and the residue were washed by water and recrystallizedby acetone-hexane to give compound 28.
Multi-step reaction with 2 steps 1: ammonia; iodine / tetrahydrofuran / 20 °C 2: hydroxylamine hydrochloride; potassium carbonate / methanol / Reflux
  • 42
  • [ 2089-36-3 ]
  • [ 4720-72-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine; fluorosulfonyl fluoride / acetonitrile / 0.5 h / 20 °C 2: hydroxylamine / acetonitrile / 3 h / Reflux
  • 43
  • [ 98-88-4 ]
  • [ 4720-72-3 ]
  • 3-(3,4-methylenedioxy)phenyl-5-phenyl-1,2,4-oxadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine In acetonitrile at 80℃; for 6h; General procedure: Following, compound 28 (1 mmol) and pyridine (1 mL) were mixedin dry ACN (5 mL). And the prepared butyryl chloride was then addedinto the mixture and heated to 80 for 6 h. The resulting mixture wasconcentrated by reduced pressure and dissolve into EtOAc (15 mL) thenpartitioned by 1 N HCl aqueous solution (3 × 10 mL) and concentratedNaHCO3 aqueous solution (3 × 10 mL), sequentially. The organiclayers were dried over anhydrous MgSO4, filtered, and concentratedunder reduced pressure. The residue was recrystallized from the solutionof CHCl3-Hex to give target compounds 29b.
  • 44
  • [ 609-65-4 ]
  • [ 4720-72-3 ]
  • 3-(3,4-methylenedioxy)phenyl-5-(2-chloro)phenyl-1,2,4-oxadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine In acetonitrile at 80℃; for 6h; General procedure: Following, compound 28 (1 mmol) and pyridine (1 mL) were mixedin dry ACN (5 mL). And the prepared butyryl chloride was then addedinto the mixture and heated to 80 for 6 h. The resulting mixture wasconcentrated by reduced pressure and dissolve into EtOAc (15 mL) thenpartitioned by 1 N HCl aqueous solution (3 × 10 mL) and concentratedNaHCO3 aqueous solution (3 × 10 mL), sequentially. The organiclayers were dried over anhydrous MgSO4, filtered, and concentratedunder reduced pressure. The residue was recrystallized from the solutionof CHCl3-Hex to give target compounds 29b.
  • 45
  • [ 141-75-3 ]
  • [ 4720-72-3 ]
  • 3-(3,4-methylenedioxy)phenyl-5-propyl-1,2,4-oxadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine In acetonitrile at 80℃; for 6h; Following, compound 28 (1 mmol) and pyridine (1 mL) were mixedin dry ACN (5 mL). And the prepared butyryl chloride was then addedinto the mixture and heated to 80 for 6 h. The resulting mixture wasconcentrated by reduced pressure and dissolve into EtOAc (15 mL) thenpartitioned by 1 N HCl aqueous solution (3 × 10 mL) and concentratedNaHCO3 aqueous solution (3 × 10 mL), sequentially. The organiclayers were dried over anhydrous MgSO4, filtered, and concentratedunder reduced pressure. The residue was recrystallized from the solutionof CHCl3-Hex to give target compounds 29b.
  • 46
  • [ 24158-88-1 ]
  • [ 4720-72-3 ]
  • (2S,5R)-2-(3-(benzo[d][1,3]dioxol-5-yl)-1,2,4-oxadiazol-5-yl)-6,6-dibromo-3,3-dimethyl-4-thia-1-azabicyclo[3.2.0]heptan-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 6,6-dibromopenicillanic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In toluene; acetonitrile at 20℃; for 1h; Stage #2: N′-hydroxybenzo[d][1,3]dioxole-5-carboximidamide In toluene; acetonitrile for 4h; Reflux;
  • 47
  • [ 4720-72-3 ]
  • [ 4421-09-4 ]
YieldReaction ConditionsOperation in experiment
70% With Imidazole hydrochloride In N,N-dimethyl-formamide at 120℃; for 2h;
  • 48
  • [ 127-19-5 ]
  • [ 4720-72-3 ]
  • 3-(benzo[d][1,3]dioxol-5-yl)-5-methyl-1,2,4-oxadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With Imidazole hydrochloride In neat (no solvent) at 100℃; for 6h; 2.2. General procedure for the synthesis of 3,5-disubstituted-1,2,4-oxadiazoles 3a-3r, 4a-4d, 5a-5c and 6a-6c. General procedure: A round-bottom flask was charged with benzamidoxime 1a (0.5 g, 3.67 mmol, 1.0 equiv.), N,N-dimethylacetamide (1 ml, excess), and imidazole hydrochloride (2.5 equiv.). The mixture was stirred at 100 °C for 6 hours. Reaction was monitored by TLC. When the reaction reached completion, a saturated solution of NaCl (20 ml) was added. After extraction of aqueous phase with ethyl acetate (3×50 mL), the organic phase was dried over anhydrous Na2SO4 and concentrated in vacuum with silica gel added. The residue was separated by chromatography (petroleum ether/ethyl acetate 150:1) to obtain the desired product 3a.
  • 49
  • [ 1642-81-5 ]
  • [ 4720-72-3 ]
  • N’-((4-(chloromethyl)benzoyl)oxy)3,4-methylenedioxyphen-1-yl-5-carboxyimidamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% Stage #1: p-(chloromethyl)benzoic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: N′-hydroxybenzo[d][1,3]dioxole-5-carboximidamide In N,N-dimethyl-formamide at 20℃; 4.1.8. Synthesis of N’-((4-(chloromethyl)benzoyl)oxy)3,4-methylenedioxyphen-1-yl-5-carboxyimidamide (12) 4-chloromethylbenzoic acid (0.28 mmol, 47 mg, 1 eq) and N,N-carbonyldiimidazole(0.56 mmol, 94 mg, 2 eq) in anhydous DMF (1 mL)were stirred at room temperature for 30 min. 3,4-methylenedioxyphenylamidoxime(0.28 mmol, 50 mg, 1 eq) was added and the reactionmaintained under stirring overnight. At the end, brine (25 mL) wasadded, and the reactional mixture was extracted with CH2Cl2:MeOH(1:1 v/v, 4 × 10 mL). The organic layers were dried over anhydrousNa2SO4, filtered, and the solvent was removed under vacuum. Theproduct was obtained as a white solid (69 mg, 74% yield) after purification(SiO2, hexane:ethyl acetate 4:6). 1H NMR (300 MHz, CDCl3): δ8.16 (d, J = 8.3, 2H), 7.60 (d, J = 8.3, 2H), 7.40 (dd, J = 1.8, 8.2, 1H),7.34 (d, J = 1.4, 1H), 6.92 (d, J = 8.2, 1H), 6.08 (s, 2H), 4.81 (s, 2H). 13CNMR (75 MHz, CDCl3): δ 163.8, 157.7, 150.6, 148.7, 143.6, 130.9,130.8, 129.6, 126.6, 122.0, 108.8, 107.8, 102.6, 46.0. HRMS-ESI: m/z[M + Na]+ Calcd for C16H13ClN2O4Na 355.0462, found 355.0481. MPC: 150.4-151.8.
  • 50
  • [ 53-86-1 ]
  • [ 4720-72-3 ]
  • 1-(4-chlorobenzoyl)-2-methyl-5-methoxy-3-[3-(1,3-benzodioxol-5-yl)-1,2,4-oxadiazol-5-yl]-methyl}-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% Stage #1: [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid With 1,1'-carbonyldiimidazole In acetonitrile at 20℃; for 0.5h; Stage #2: N′-hydroxybenzo[d][1,3]dioxole-5-carboximidamide In acetonitrile for 3h; Stage #3: In acetonitrile for 24h; Reflux; 5.2. General procedure for the synthesis of 1-(4-chlorobenzoyl)-2-methyl-5-methoxy-3-[(3-aryl-1,2,4-oxadiazol-5-yl)methyl]-1H-indole (5a-g) General procedure: To a solution of indomethacin 1 (1.5 mmole, 0.53 g) in 30 mlacetonitrile, the N,N’-carbonyldiimidazole CDI (11 mmole, 1.2 g) wasadded and the mixture was stirred at room temperature for 30 mins. Therespective amidoximes 3a-g (10 mmole) was then added and stirred for further 3 hrs. After that, the reaction mixture was heated at reflux for 24hrs (monitored with TLC) and cooled to room temperature. The formedprecipitate was collected by filtration, dried and recrystallized fromethanol to give compounds 5a-g.
  • 51
  • [ 53-86-1 ]
  • [ 4720-72-3 ]
  • N'-{2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetoxy}-1,3-benzodioxole-5-carboximidamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% Stage #1: [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid With 1,1'-carbonyldiimidazole In acetonitrile at 20℃; for 0.5h; Stage #2: N′-hydroxybenzo[d][1,3]dioxole-5-carboximidamide In acetonitrile at 20℃; for 3h; 5.1. General procedure for the synthesis of N’-{2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetoxy}arylcarboximidamide (4a-g) General procedure: To a solution of indomethacin 1 (1.5 mmole, 0.53 g) in 30 mlacetonitrile, the N,N’-carbonyldiimidazole CDI (11 mmole, 1.2 g) wasadded and the mixture was stirred at room temperature for 30 mins. Therespective amidoximes 3a-g (10 mmole) was then added and stirred forfurther 3 hrs. After completion of reaction (monitored with TLC), theformed precipitate was collected by filtration, washed several times withacetonitrile, dried and used without further purification to give 3a-g.
  • 52
  • [ 4720-72-3 ]
  • [ 704-91-6 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
55% Stage #1: 1H-indazole-6-carboxylic acid With 1-hydroxy-7-aza-benzotriazole; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: (Z)-N'-hydroxybenzo[d][1,3]dioxole-5-carboximidamide In N,N-dimethyl-formamide at 20℃; for 24h; 4.1.1. General procedures for the synthesis of amidoximes 6a-v General procedure: To a solution of 1H-indazole-6-carboxylic acid 5 (1 mmol) in DMF (5 mL), EDC (1.3 mmol) and HOAt (1 mmol) were added. The amidoximes 3a-v (1 mmol) were added after 30 min of stirring at room temperature. The resulting mixture was stirred for 24 h at room temperature. The mixture was extracted with EtOAc after adding 30 mL of water, washed three times with water, and once with brine. The mixed organic layer was dried with Na2SO4 and then evaporated at reduced pressure. Finally, using silica gel column chromatography, the resulting compounds 6a-v were purified and isolated as white powders in 50-70% yields. 4.1.2. (Z)-N’-[(1H-indazole-6-carbonyl) oxy]benzo[d][1,3]dioxole-5-carboximidamide (6a) Yield 55%, white solid, m.p. 223-225 °C. 1H NMR (400 MHz, DMSO-d6) δ 13.47 (s, 1H), 8.38 (s, 1H), 8.21 (s, 1H), 7.89 (s, 2H), 7.35 (dd, J = 8.1, 1.5 Hz, 1H), 7.31 (d, J = 1.4 Hz, 1H), 7.03 (d, J = 8.1 Hz,1H), 6.92 (s, 2H), 6.11 (s, 2H). 13C NMR (101 MHz, DMSO-d6) δ 164.05, 156.59, 149.08, 147.24, 139.24, 133.70, 126.96, 125.39, 125.22,121.25, 120.69, 120.51, 112.46, 108.10, 107.00, 101.53. HRMS (EI): calcd. for C16H12N4NaO4 [M + Na]+: m/z 347.0756; found: m/z 347.0761.
55% Stage #1: 1H-indazole-6-carboxylic acid With 1-hydroxy-7-aza-benzotriazole; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: (Z)-N'-hydroxybenzo[d][1,3]dioxole-5-carboximidamide In N,N-dimethyl-formamide at 20℃; for 24h; 4.1.1. General procedures for the synthesis of amidoximes 6a-v General procedure: To a solution of 1H-indazole-6-carboxylic acid 5 (1 mmol) in DMF (5 mL), EDC (1.3 mmol) and HOAt (1 mmol) were added. The amidoximes 3a-v (1 mmol) were added after 30 min of stirring at room temperature. The resulting mixture was stirred for 24 h at room temperature. The mixture was extracted with EtOAc after adding 30 mL of water, washed three times with water, and once with brine. The mixed organic layer was dried with Na2SO4 and then evaporated at reduced pressure. Finally, using silica gel column chromatography, the resulting compounds 6a-v were purified and isolated as white powders in 50-70% yields. 4.1.2. (Z)-N’-[(1H-indazole-6-carbonyl) oxy]benzo[d][1,3]dioxole-5-carboximidamide (6a) Yield 55%, white solid, m.p. 223-225 °C. 1H NMR (400 MHz, DMSO-d6) δ 13.47 (s, 1H), 8.38 (s, 1H), 8.21 (s, 1H), 7.89 (s, 2H), 7.35 (dd, J = 8.1, 1.5 Hz, 1H), 7.31 (d, J = 1.4 Hz, 1H), 7.03 (d, J = 8.1 Hz,1H), 6.92 (s, 2H), 6.11 (s, 2H). 13C NMR (101 MHz, DMSO-d6) δ 164.05, 156.59, 149.08, 147.24, 139.24, 133.70, 126.96, 125.39, 125.22,121.25, 120.69, 120.51, 112.46, 108.10, 107.00, 101.53. HRMS (EI): calcd. for C16H12N4NaO4 [M + Na]+: m/z 347.0756; found: m/z 347.0761.
  • 53
  • [ 4743-58-2 ]
  • [ 4720-72-3 ]
  • C18H12N2O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1,1′-carbonyldiimidazole In N,N-dimethyl-formamide at 90℃;
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Benzo[d][1,3]dioxole-5-carboximidamide

Similarity: 0.88

Chemical Structure| 80531-15-3

[ 80531-15-3 ]

Benzo[d][1,3]dioxole-5-carboximidamide hydrochloride

Similarity: 0.86

Chemical Structure| 95933-72-5

[ 95933-72-5 ]

N,3,4-Trihydroxybenzimidamide

Similarity: 0.82

Chemical Structure| 17353-82-1

[ 17353-82-1 ]

4,4'-Oxybis(N-hydroxybenzimidamide)

Similarity: 0.80

Oximes

Chemical Structure| 95933-72-5

[ 95933-72-5 ]

N,3,4-Trihydroxybenzimidamide

Similarity: 0.82

Chemical Structure| 17353-82-1

[ 17353-82-1 ]

4,4'-Oxybis(N-hydroxybenzimidamide)

Similarity: 0.80

Related Parent Nucleus of
[ 4720-72-3 ]

Other Aromatic Heterocycles

Chemical Structure| 4720-71-2

[ 4720-71-2 ]

Benzo[d][1,3]dioxole-5-carboximidamide

Similarity: 0.88

Chemical Structure| 80531-15-3

[ 80531-15-3 ]

Benzo[d][1,3]dioxole-5-carboximidamide hydrochloride

Similarity: 0.86