2-(Trifluoroacetyl)imidazoles, 2-Trifluoroacetyl-1,3-thi­azoles, and 2-Trifluoroacetyl-1,3-oxazoles

Pavel V. Khodakovskiy; Dmitriy M. Volochnyuk; Dmitriy M. Panov; Igor I. Pervak; Evgenij V. Zarudnitskii; Oleg V. Shishkin; Aleksandr A. Yurchenko; Alexander Shivanyuk; Andrey A. Tolmachev

doi:10.1055/s-2008-1032197

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Synthesis 2008(6): 948-956
DOI: 10.1055/s-2008-1032197

PAPER

2-(Trifluoroacetyl)imidazoles, 2-Trifluoroacetyl-1,3-thiazoles, and 2-Trifluoroacetyl-1,3-oxazoles

Pavel V. Khodakovskiy^a,b, Dmitriy M. Volochnyuk*^a,c, Dmitriy M. Panov^a,b, Igor I. Pervak^c, Evgenij V. Zarudnitskii^c, Oleg V. Shishkin^d, Aleksandr A. Yurchenko^c, Alexander Shivanyuk^a,b, Andrey A. Tolmachev^a,b
^a Enamine Ltd., 23 A. Matrosova st., 01103 Kiev, Ukraine
Fax: +380(44)5373253; e-Mail: D.Volochnyuk@enamine.net;
^b National Taras Shevchenko University, 62 Volodymyrska st., 01033 Kiev-33, Ukraine
^c Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska 5, 02094 Kiev-94, Ukraine
^d Institute for Scintillation Materials, National Academy of Science of Ukraine, 60 Lenina ave., 61001 Kharkiv, Ukraine

Further Information

Publication History

Received 15 November 2007
Publication Date:
28 February 2008 (online)

Abstract
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Abstract

A facile method of trifluoroacylation of imidazoles, 1,3-thiazoles, and 1,3-oxazoles with trifluoroacetic anhydride resulted in a set of heterocyclic trifluoromethyl-containing ketones. Unlike common ketones, these compounds form stable hydrates and enter into noncatalytic ene reactions with terminal olefins affording the corresponding allyl alcohols.

Key words

fluorine compounds - acylations - ketones - nitrogen-containing heterocycles - stable hydrates

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