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 language | English |
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Pages (from-to) | 742-753 |
Number of pages | 12 |
Journal | Chemistry of Heterocyclic Compounds |
Volume | 46 |
Issue number | 6 |
DOIs | |
Publication status | Published - Oct 2010 |
Externally published | Yes |
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