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Oxidative cyclization of 2-amino-1-arylideneaminobenzimidazoles into 1,2,4-triazolo[1,5-a]benzimidazoles

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

When heated in nitrobenzene, 1-arylideneamino-2-methylaminobenzimidazoles convert in a 20...30% yield into 2-aryl-3-methyl-1,2,4-triazolo[1,5-a]benzimidazoles. In addition, 2-methylaminobenzimidazole and the corresponding benzonitrile are formed as a result of a thermal splitting of the N-N bond. Under the same conditions, 2-amino-1-arylideneaminobenzimidazoles and 1-arylideneamino-3-methylbenzimidazoline-2-imines give only products of splitting off of the nitrile. In several cases, the subsequent reaction of the nitrile with 2-amino-1-methylbenzimidazole leads to the formation of benzamidines.

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Authors and Affiliations

  1. Scientific Research Institute of Physical and Organic Chemistry, M. A. Suslov State University, 344071, Rostov-on-Don

    T. A. Kuz'menko, V. V. Kuz'menko, A. F. Pozharskii & N. A. Klyuev

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  1. T. A. Kuz'menko
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  2. V. V. Kuz'menko
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  3. A. F. Pozharskii
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  4. N. A. Klyuev
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1226–1231, September, 1988.

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Kuz'menko, T.A., Kuz'menko, V.V., Pozharskii, A.F. et al. Oxidative cyclization of 2-amino-1-arylideneaminobenzimidazoles into 1,2,4-triazolo[1,5-a]benzimidazoles. Chem Heterocycl Compd 24, 1012–1017 (1988). https://doi.org/10.1007/BF00474046

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  • DOI: https://doi.org/10.1007/BF00474046

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