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

被引：27

作者：

Muzalevskiy, Vasiliy M. ^{[1
]}

Nenajdenko, Valentine G. ^{[1
]}

Shastin, Aleksey V. ^{[2
]}

Balenkova, Elizabeth S. ^{[1
]}

Haufe, Guenter ^{[3
]}

机构：

[1] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119992, Russia

[2] Inst Problems Chem Phys, Chernogolovka 142432, Moscow Region, Russia

[3] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany

来源：

SYNTHESIS-STUTTGART | 2009年 / 13期

基金：

俄罗斯基础研究基金会;

关键词：

alkenes; alkynes; ethers; fluorine; heterocycles; nucleophilic substitution; STEREOSELECTIVE-SYNTHESIS; EFFICIENT SYNTHESIS; KETONES; METALATION; ALDEHYDES; ALCOHOLS;

D O I：

10.1055/s-0029-1216697

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

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.

引用

页码：2249 / 2259

页数：11

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