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Research on imidazo[1,2-a]benzimidazole derivatives

VIII. 1H- and 1-methyl-2-phenylimidazo[1,2-a]benzimidazoles and their reactivities

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

1H-2-Phenyl- and 1-methyl-2-phenylimidazo[1,2-a]benzimidazoles were synthesized by the action of phenacyl bromide on 2-amino- and 2-methylaminobenzimidazoles and subsequent cyclization of the resulting 1-phenacyl derivatives. The reactivities of the compounds obtained with respect to electrophilic substitution reactions were studied. It is shown that bromination proceeds in the 3 position of the imidazole ring, while hydroxymethylation proceeds in the benzene ring of the heterocycle. Calculations by the LCAO MO method within the π-electron approximation for the 1H and 9H tautomers of 2-phenylimidazo[1,2-a]-benzimidazole, which are in complete agreement with the experimental data, are presented.

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Authors and Affiliations

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

    V. A. Anisimova, A. M. Simonov & A. F. Pozharskii

Authors
  1. V. A. Anisimova
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  2. A. M. Simonov
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  3. A. F. Pozharskii
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Additional information

See [1] for communication VII.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 797–802, June, 1973

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Anisimova, V.A., Simonov, A.M. & Pozharskii, A.F. Research on imidazo[1,2-a]benzimidazole derivatives. Chem Heterocycl Compd 9, 731–735 (1973). https://doi.org/10.1007/BF00472318

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  • DOI: https://doi.org/10.1007/BF00472318

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