Interaction of (z)-4-bromo-1,3-di(2-thienyl)- 2-buten-1-one with amines, synthesis of di(2-thienyl)azolo[a]pyridines

L. M. Potikha, A. R. Turelyk, V. A. Kovtunenko, A. V. Turov, G. V. Palamarchuk, R. I. Zubatyuk, O. V. Shishkin

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2 Citations (Scopus)

Abstract

(Z)-4-Bromo-1,3-di(2-thienyl)-2-buten-1-one was obtained by the bromination of 1,3-di(2-thienyl)-2-buten-1-one by NBS in anhydrous CCl4. The starting butanone was obtained by the condensation of 1-(2-thienyl)-1-ethanone by the action of SOCl2. The reaction of (Z)-4-bromo-1,3-di(2-thienyl) -2-buten-1-one with tertiary amines such as Et3N, pyridine, 1-alkyl-1,3-diazole, 1-alkylbenzimidazole, and 1-alkyl-1,2,4-triazole leads to quaternary salts. The azolium salts cyclize by the action of base to give di(2-thienyl)azolo[a]pyridinium derivatives. 3-Methyl-6,8-di(2-thienyl)[1,3] thiazolo[3,2-a]pyridin-4-ium and 2,4-di(2-thienyl)pyrido[2,1-b]benzothiazol-10- ium bromides were obtained by the same procedure but without separating the intermediate quaternary salts.

Original languageEnglish
Pages (from-to)742-753
Number of pages12
JournalChemistry of Heterocyclic Compounds
Volume46
Issue number6
DOIs
Publication statusPublished - Oct 2010
Externally publishedYes

Keywords

  • 4-bromo-1,3-di(2-thienyl)-2-buten-1-one
  • [1,2,4]triazolo[4,3-a]pyridine
  • [1,3]benzothiazolo[3,2-a] pyridine
  • imidazo[1,2-a]pyridine
  • pyrido[1,2-a]benzimidazole
  • pyrido[2,1-b]benzothiazole

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