o-Phenylenediamine as a Source of Fused Azole, Azine, and Diazepine Derivatives

A facile synthetic approach to diazepine and/or benzimidazole derivatives has been developed through the reaction of enamine [ N 1 -(1-phenylethenyl)benzene-1,2-diamine] obtained from o -phenylenediamine and acetophenone. Its reaction with isophthaloyl chloride produced bis(1,5-benzodiazepinyl)benze...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2021-07, Vol.57 (7), p.1152-1157
Main Authors: Shehta, W., Assy, M. G., Ismail, N. A., Almostafa, A. M.
Format: Article
Language:English
Subjects:
Acetophenone
Benzene
Benzodiazepines
Benzotriazole
Carbon
Carbon disulfide
Chemistry
Chemistry and Materials Science
Chlorides
Diamines
Hydrocarbons
Nitrogen
Organic Chemistry
Phenylenediamine
Sodium nitrite
Thiocyanates
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Summary:A facile synthetic approach to diazepine and/or benzimidazole derivatives has been developed through the reaction of enamine [ N 1 -(1-phenylethenyl)benzene-1,2-diamine] obtained from o -phenylenediamine and acetophenone. Its reaction with isophthaloyl chloride produced bis(1,5-benzodiazepinyl)benzene derivative via cyclization involving the nucleophilic enamino carbon atom, whereas the cyclocondensation with diethyl succinate occurred at the nucleophilic nitrogen atom to give bis-benzimidazole derivative. Depending on the conditions, the cyclization with carbon disulfide in DMSO afforded tricyclic 4-phenylimidazo[4,5,1- hi ]indole-2(1 H )-thione, while 4-phenyl-1,3-dihydro-2 H -1,5-benzodiazepine-2-thione was formed in the presence of pyridine. Cyclocondensation of o -phenylenediamine with two equivalents of acetophenone in acid medium produced 3-phenyl-1-(1-phenylethenyl)-1,4-dihydroquinoxaline. N -(2-Aminophenyl)thiourea obtained from o -phenylenediamine and ammonium thiocyanate reacted with chloroacetyl chloride, diethyl malonate, carbon disulfide, and sodium nitrite in aqueous HCl to afford benzimidazole, thiadiazolobenzimidazole, and benzotriazole derivatives.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428021070150