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

  • L. M. Potikha
  • A. R. Turelyk
  • V. A. Kovtunenko
Article

DOI: 10.1007/s10593-011-0829-6

Cite this article as:
Potikha, L.M., Turelyk, A.R. & Kovtunenko, V.A. Chem Heterocycl Comp (2011) 47: 745. doi:10.1007/s10593-011-0829-6

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.

Keywords

azepino[1,2-a]benzimidazole γ-bromodypnone imidazo[1,2-a]azepine cyclization 

Copyright information

© Springer Science+Business Media, Inc. 2011

Authors and Affiliations

  • L. M. Potikha
    • 1
  • A. R. Turelyk
    • 1
  • V. A. Kovtunenko
    • 1
  1. 1.Taras Shevcheko National UniversityKievUkraine

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