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Synthesis 2010(6): 979-984  
DOI: 10.1055/s-0029-1218633
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Noncatalytic Electrophilic Oxyalkylation of Some Five-Membered Heterocycles with 2-(Trifluoroacetyl)-1,3-azoles

Pavel V. Khodakovskiya,b, Pavel K. Mykhailiuk*a,b, Dmitriy M. Volochnyuka,c, Andrey A. Tolmacheva,b
a Enamine Ltd., Oleksandra Matrosova St. 23, 01103 Kyiv, Ukraine
b Department of Chemistry, Kyiv National Taras Shevchenko University, Volodymyrska St. 64, 01033 Kyiv, Ukraine
c Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska St. 5, 02660 Kyiv-94, Ukraine
Fax: +380(44)2351273; e-Mail: Pashamk@gmx.de;
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Publication History

Received 18 November 2009
Publication Date:
04 January 2010 (online)

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Abstract

A set of electrophilic 2-(trifluoroacetyl)-1,3-azoles demonstrated­ excellent activity in the C-oxyalkylation of pyrrole, furan, thiophene, 1,3-thiazole, and 1,2-oxazole derivatives. The reaction conditions and the yields of the corresponding trifluoromethyl-substituted alcohols depend strongly on both the electronic and steric nature of the 1,3-azole unit.

Key words

Friedel-Crafts alkylation - trifluoromethyl alcohols - heterocycles - pyrroles - furans

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