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Studies of imidazo[1,2-a]benzimidazole derivatives. 21. Synthesis of haloketones in the imidazo[1,2-a] benzimidazole series

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Methods for the synthesis of imidazo[1,2-a]benzimidazole haloketone derivatives have been investigated. It has been found that α-bromoketone derivatives of this heterocycle can be prepared either by bromination of 3-acylimidazo[1,2-a]benz-imidazoles with bromine in glacial acetic acid or by acylation of 3-unsubstituted imidazo[1,2-a]benzimidazoles with haloanhydride derivatives of α-bromoalkanoic acids. Treatment of imidazo[1,2-a]benzimidazoles with 3-chloropropionyl chloride results in the formation of imidazo[1,2-a]benzimidazolyl-3-propionyl chloride and bis(imidazo[1,2-a]benzimidazolyl)propan-3-one derivatives as side products. Reaction of 2-phenylimidazo[1,2-a]benzimidazoles with 3-bromopropionic acid in polyphosphoric acid gives benzocyclohepten[5′,6′:4,5]imidazo[1,2-a]benzimidazole 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, T. B. Korochina, N. I. Avdyunina & A. M. Simonov

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  1. V. A. Anisimova
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  2. T. B. Korochina
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  3. N. I. Avdyunina
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  4. A. M. Simonov
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Additional information

For Communication 20, see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 339–345, March, 1986.

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Anisimova, V.A., Korochina, T.B., Avdyunina, N.I. et al. Studies of imidazo[1,2-a]benzimidazole derivatives. 21. Synthesis of haloketones in the imidazo[1,2-a] benzimidazole series. Chem Heterocycl Compd 22, 275–282 (1986). https://doi.org/10.1007/BF00514994

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  • DOI: https://doi.org/10.1007/BF00514994

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