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Synthesis and Cyclization of 2-Amino- and 2-Methyl-Substituted 1,3-Diaminobenzimidazolium Salts

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Chemistry of Heterocyclic Compounds Aims and scope

N-Amination of 1-amino(alkylamino, benzylidenamino)-substituted 2-amino- and 2-methylbenzimid-azoles with O-picrylhydroxylamine gave the respective 1,2,3-triamino- and 1,3-diamino-2-methylbenz-imidazolium salts, which cyclized upon treatment with acetic anhydride/K2CO3 into previously unreported derivatives of N-amino[1, 2, 4]triazolo[1,5-а]benzimidazoles and N-aminopyrazolo-[1,5-а]benzimidazoles. The presence of С-acetyl substituent in the formed pyrazolo[1,5-а]benz-imidazoles was interpreted by quantum-chemical calculations as resulting from acylation of the intermediate methylene base, not tricyclic system.

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This work was performed within the framework of project part of the State Assignment for scientific activity (Project No. 4.196.2014/K), with equipment at the Collective Use Center "Molecular Spectroscopy" of the Southern Federal University.

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Authors and Affiliations

  1. Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 Stachki Ave., Rostov-on-Don, 344090, Russia

    T. A. Kuz’menko, A. S. Morkovnik, L. N. Divaeva & G. S. Borodkin

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  1. T. A. Kuz’menko
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  2. A. S. Morkovnik
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  3. L. N. Divaeva
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Correspondence to A. S. Morkovnik.

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(V. V. Kuz’menko) Deceased.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1714–1724, November, 2014.

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Kuz’menko, T.A., Morkovnik, A.S., Divaeva, L.N. et al. Synthesis and Cyclization of 2-Amino- and 2-Methyl-Substituted 1,3-Diaminobenzimidazolium Salts. Chem Heterocycl Comp 50, 1575–1585 (2015). https://doi.org/10.1007/s10593-014-1627-8

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