INTERACTION OF (<i>Z</i>)-4-BROMO-1,3-DI(2-THIENYL)- 2-BUTEN-1-ONE WITH AMINES, SYNTHESIS OF DI(2-THIENYL)AZOLO[<i>a</i>]PYRIDINES

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.

How to Cite
Potikha, L. M.; Turelyk, A. R.; Kovtunenko, V. A.; Turov, A. V.; Palamarchuk, G. V.; Zubatyuk, R. I.; Shishkin, O. V. Chem. Heterocycl. Compd. 2010, 46, 742. [Khim. Geterotsikl. Soedin. 2010, 919.]

For this article in the English edition see DOI 10.1007/s10593-010-0578-y