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DOI: 10.1055/s-0029-1216697
Synthetic Approach to Alkoxy-β-(trifluoromethyl)styrenes and Their Application in the Synthesis of New Trifluoromethylated Heterocycles
Publication History
Publication Date:
12 May 2009 (online)
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Abstract
A new convenient stereoselective pathway to alkoxy-β-(trifluoromethyl)styrenes is described. Reactions of β-chloro- and β-bromo-β-(trifluoromethyl)styrenes with sodium methoxide and potassium tert-butoxide led to methoxy- and tert-butoxy-β-(trifluoromethyl)styrenes in good to excellent yields. Bromination of tert-butoxy-β-(trifluoromethyl)styrenes proceeded with formation of aryl(bromo)methyl trifluoromethyl ketones. The latter compounds were found to be useful starting materials for the synthesis of different heterocyclic compounds bearing a trifluoromethyl group. In this way trifluoromethylated derivatives of imidazopyridine, imidazopyrimidine, imidazobenzimidazole, imidazothiazole, thiazole, and aminothiazole were obtained in moderate to high yield.
Key words
alkenes - alkynes - ethers - fluorine - heterocycles - nucleophilic substitution
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