New method for the annelation of a pyridine ring on derivatives of imidazole and benzimidazole

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

Research output: Contribution to journalArticleResearchpeer-review

1 Citation (Scopus)

Abstract

The interaction of (Z)-1,3-diaryl-4-bromo-2-buten-1-ones with 1-substituted (benz)imidazoles in benzene gave (Z)-1-R-3-(2,4-diaryl-4-oxo-2-butenyl)-1H- imidazolium bromides and (Z)-1-R-3-(2,4-diaryl-4-oxo-2-butenyl)-1H- benzimidazolium bromides which readily cyclize in the presence of base to form derivatives of 7,9-diarylpyrido[1,2-a]benzimidazole and 6,8-diarylpyrimidazo[1, 2-a]pyridine. The effects of the nature of substituents in the benzene ring of the diarylbutenones and the substituent at N(1) in the (benz)imidazoles on the alkylation and cyclization reactions has been studied. The optimum conditions for the synthesis of the 5-R-4-hydroxy-2,4-diphenyl-4,5-dihydro-1H-pyrido[1,2-a] benz-imidazol-10-ium, 5-R-2,4-diaryl-4-hydroxy-4,5-dihydro-3H-pyrido[1,2-a] benzimidazol-10-ium, and 5-R-2,4-diaryl-5H-pyrido[1,2-a]benzimidazol-10-ium have been found.

Original languageEnglish
Pages (from-to)82-95
Number of pages14
JournalChemistry of Heterocyclic Compounds
Volume46
Issue number1
DOIs
Publication statusPublished - May 2010
Externally publishedYes

Keywords

  • γ-bromodypnone
  • Cyclization of azolium ylides
  • Imidazo[1,2-a]pyridine
  • Pyrido[1,2-a]benzimidazole

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