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

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Abstract

A facile synthetic approach to diazepine and/or benzimidazole derivatives has been developed through the reaction of enamine [N1-(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(1H)-thione, while 4-phenyl-1,3-dihydro-2H-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.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Zagazig University, 44519, Zagazig, Egypt

    W. Shehta, M. G. Assy, N. A. Ismail & A. M. Almostafa

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  1. W. Shehta
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  2. M. G. Assy
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  3. N. A. Ismail
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Shehta, W., Assy, M.G., Ismail, N.A. et al. o-Phenylenediamine as a Source of Fused Azole, Azine, and Diazepine Derivatives. Russ J Org Chem 57, 1152–1157 (2021). https://doi.org/10.1134/S1070428021070150

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  • DOI: https://doi.org/10.1134/S1070428021070150

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