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Synthesis 2005(8): 1269-1278  
DOI: 10.1055/s-2005-865290
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Convenient Synthesis and Chemical Properties of 3-Acylamino-6-poly­fluoroalkyl-2H-pyran-2-ones

Igor I. Gerus*a, Nataliya A. Tolmachovaa, Sergey I. Vdovenkoa, Roland Fröhlichb, Günter Haufe*b
a Institute of Bioorganic Chemistry and Petrochemistry NASU, Murmanska 1, 02094 Kiev, Ukraine
Fax: +38(44)5732552; e-Mail: igerus@hotmail.com;
b Organisch-Chemisches Institut der Universität Münster, Corrensstraße 40, 48149 Münster, Germany
Fax: +49(251)8339772; e-Mail: haufe@uni-muenster.de;
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Publikationsverlauf

Received 10 November 2004
Publikationsdatum:
07. April 2005 (online)

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Abstract

A number of 3-acylamino-6-polyfluoroalkyl-2H-pyran-2-ones 3 were synthesized from β-alkoxyvinyl polyfluoroalkyl ketones 1 and N-acylglycines 2 in acetic anhydride in high yield. The reactions of trifluoromethyl-containing 2H-pyran-2-one 3b with O- and N-nucleophiles were studied and 3-N-benzoylamino-6-hydroxy-6-trifluoromethyl-5,6-dihydro-2H-pyran-2-one (13), 3-N-benzoylamino-6-hydroxy-6-trifluoromethyl-5,6-dihydro-2H-pyridin-2-one (14a), and N- and O-substituted 3-(N-benzoylamino)-6-trifluoromethyl-2H-pyridin-2-ones (15c,e, and 16) were synthesized.

Key words

enones - heterocycles - 2H-pyran-2-ones - 2H-pyridin-2-ones - aminations - alkylations - trifluoromethyl

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