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1-Amino-3-alkyl-2-(methylthio)benzimidazolium salts: synthesis, reaction with CH-acid anions, and conversion to pyrazolo[1,5-a]benzimidazole derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

For the first time, 1-amino-3-alkylbenzimidazolinethiones were obtained by heating 1-amino-3-alkylbenzimidazolium iodides with sulfur in the presence of triethylamine. They were converted to 1-amino-3-alkyl-2-(methylthio)benzimidazolium salts, which, during reaction with CH-acid onions, gave the corresponding 1-amino-3-alkyl-2-methylenebenzimidazoline derivatives. Under conditions of alkaline or acid catalysis, the latter derivatives cyclized to 2-amino- or 2-hydroxy derivatives of pyrazolo[1,5-a]benzimidazole.

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Authors and Affiliations

  1. Scientific-Research Institute of Physical and Organic Chemistry, Rostov State University, 344006, Rostov-on-Don

    T. A. Kuz'menko, V. V. Kuz'menko, A. F. Pozharskii, O. V. Kryshtalyuk & G. G. Aleksandrov

Authors
  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. O. V. Kryshtalyuk
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  5. G. G. Aleksandrov
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 205–214, February, 1992.

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Kuz'menko, T.A., Kuz'menko, V.V., Pozharskii, A.F. et al. 1-Amino-3-alkyl-2-(methylthio)benzimidazolium salts: synthesis, reaction with CH-acid anions, and conversion to pyrazolo[1,5-a]benzimidazole derivatives. Chem Heterocycl Compd 28, 167–176 (1992). https://doi.org/10.1007/BF00473938

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  • DOI: https://doi.org/10.1007/BF00473938

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