Interaction of (z)-4-bromo-1,3-di(2-thienyl)- 2-buten-1-one with amines,synthesis of di(2-thienyl)azolo[a]pyridines |
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Authors: | 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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Affiliation: | (1) Taras Shevchenko Kiev National University, Kiev, Ukraine, 01033;(2) Institute for Single Crystals, National Academy of Sciences of Ukraine, Kharkiv, 61001, Ukraine |
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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. |
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