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Synthesis of azepino[1,2-a]benzimidazoles and imidazo[1,2-a]azepines

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Chemistry of Heterocyclic Compounds Aims and scope

Fusion of 4-bromo-1,3-diphenyl-2-buten-1-ones (γ-bromodypnones) with 1,2-dimethyl-1H-benzimidazole and further treatment of the reaction product with a base (morpholine) gives 7,9-diaryl-5-methyl5,10-dihydroazepino[1,2-a]benzimidazol-11-ium bromides. The reaction of γ-bromodypnone with 1-alkyl-2-methyl-1H-imidazoles in benzene at 25 °C gives quaternary azolium salts. Upon heating their solutions in alcohol in the presence of K2CO3 the latter cyclize to 1-R-6,8-diaryl-1,5-dihydroimidazo[1,2-a]azepin-4-ium bromides or 1-R-6,8-diaryl-1H-imidazo[1,2-a]azepines depending on the nature of the substituent in the benzene rings and the substituent at the N(1) atom of the imidazole.

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Authors and Affiliations

  1. Taras Shevcheko National University, 64 Volodymyrska St., Kiev, 01033, Ukraine

    L. M. Potikha, A. R. Turelyk & V. A. Kovtunenko

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  1. L. M. Potikha
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  2. A. R. Turelyk
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  3. V. A. Kovtunenko
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Correspondence to L. M. Potikha.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 901–912, June 2011.

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Potikha, L.M., Turelyk, A.R. & Kovtunenko, V.A. Synthesis of azepino[1,2-a]benzimidazoles and imidazo[1,2-a]azepines. Chem Heterocycl Comp 47, 745–754 (2011). https://doi.org/10.1007/s10593-011-0829-6

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