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Synthesis 2008(20): 3245-3252  
DOI: 10.1055/s-0028-1083150
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Baylis-Hillman Reactions of 2-(Trifluoroacetyl)-1,3-azoles

Pavel V. Khodakovskiya,b, Dmitriy M. Volochnyuk*a,c, Alexander Shivanyuka,b, Oleg V. Shishkind, Andrey A. Tolmachevb
a Enamine Ltd., 23 A. Matrosova st., 01103 Kyiv, Ukraine
Fax: +380(44)5373253; e-Mail: D.Volochnyuk@enamine.net;
b National Taras Shevchenko University, 62 Volodymyrska st., 01033 Kyiv-33, Ukraine
c Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska 5, 02094 Kyiv-94, Ukraine
d Institute for Scintillation Materials, National Academy of Sciences of Ukraine, 60 Lenina Avenue, 61001 Kharkiv, Ukraine
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Publikationsverlauf

Received 8 May 2008
Publikationsdatum:
25. September 2008 (online)

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Abstract

2-(Trifluoroacetyl)-1,3-azoles readily react with methyl acrylate and acrylonitrile under Baylis-Hillman reaction conditions to afford heterocyclic trifluoromethyl-containing allylic alcohols in 36-97% yields. The thus obtained Baylis-Hillman adducts readily undergo Michael addition reactions with various nucleophiles.

Key words

Baylis-Hillman reaction - 1,3-azoles - Michael additions - trifluoromethyl substituted - allylic alcohols

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