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Synthesis 2009(13): 2249-2259  
DOI: 10.1055/s-0029-1216697
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Vasiliy M. Muzalevskiya, Valentine G. Nenajdenko*a, Aleksey V. Shastinb, Elizabeth S. Balenkovaa, Günter Haufe*c
a Moscow State University, Department of Chemistry, Leninskie Gory, Moscow 119992, Russia
e-Mail: nen@acylium.chem.msu.ru;
b Institute of Problems of Chemical Physics, Chernogolovka, Moscow Region 142432, Russia
e-Mail: shastin@icp.ac.ru;
c Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, 48149 Münster, Germany
Fax: +49(251)8339772; e-Mail: haufe@uni-muenster.de;
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Publikationsverlauf

Received 29 December 2008
Publikationsdatum:
12. Mai 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