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Synthetic Approach to Alkoxy-beta-(trifluoromethyl)styrenes and Their Application in the Synthesis of New Trifluoromethylated Heterocycles

  作者 MUZALEVSKIY VASILIY M; NENAJDENKO VALENTINE G; SHASTIN ALEKSEY V; BALENKOVA ELIZABETH S; HAUFE GUENTER  
  选自 期刊  Synthesis;  卷期  2009年-13;  页码  2249-2259  
  关联知识点  
 

[摘要]A new convenient stereoselective pathway to alkoxy-beta-(trifluoromethyl)styrenes is described. Reactions of beta-chloro- and beta-bromo-beta-(trifluoromethyl)styrenes with sodium methoxide and potassium tert-butoxide led to methoxy- and terl-butoxy-beta-(trifluoromethyl)styrenes in good to excellent yields. Bromination of tertbutoxy-[3-(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.

 
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