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Research on imidazo[1,2-a]benzimidazole derivatives. 23. Syntheses based on 2-(2-hydroxyethylamino)benzimidazoles

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The possibility of annelation of the imidazoline ring on the basis of 2(2-hydroxyethylamino)-benzimidazoles was studied. It was shown that the action of hydrobromic, sulfuric, nitrosylsulfuric, and polyphosphoric acids, acetic anhydride, and phosphorus oxychloride on them does not lead to 2,3-dihydroimidazo[1,2-a]-benzimidazoles. In the case of POCl3 the products were 2-(2-chloroethylamino)benzimidazoles, treatment of which with alcoholic alkali led primarily to nucleophilic substitution of the chlorine atom by a methoxy group. Three-ring imidazolines are formed in 12–15% yields in this case. It was established that the reaction proceeds through the intermediate formation of aziridine derivatives.

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Authors and Affiliations

  1. Scientific-Research Institute of Physical and Organic Chemistry, M. A. Suslov Rostov State University, 344090, Rostov-on-Don

    V. A. Anisimova & M. V. Levchenko

Authors
  1. V. A. Anisimova
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  2. M. V. Levchenko
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Additional information

See [1] for communication 22.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 59–63, January, 1987.

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Anisimova, V.A., Levchenko, M.V. Research on imidazo[1,2-a]benzimidazole derivatives. 23. Syntheses based on 2-(2-hydroxyethylamino)benzimidazoles. Chem Heterocycl Compd 23, 48–52 (1987). https://doi.org/10.1007/BF00475473

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  • DOI: https://doi.org/10.1007/BF00475473

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