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Synthesis 2007(24): 3797-3806  
DOI: 10.1055/s-2007-990891
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of New Polyfluoroalkyl-Containing Pyrones, Pyridones and Pyrido[1,2-a]benzazoles from Fluorinated β-Alkoxyenones

Nataliya A. Tolmachovaa, Igor I. Gerus*a, Sergey I. Vdovenkoa, Günter Haufe*b, Yuriy A. Kirzhnerc
a Institute of Bioorganic Chemistry and Petrochemistry NASU, Murmanskaya 1, 03660 Kiev-94, Ukraine
Fax: +38(044)5732552; e-Mail: igerus@hotmail.com;
b Organisch-Chemisches Institut, Universität Münster, Corrensstraße 40, 48149 Münster, Germany
Fax: +49(251)8339772; e-Mail: haufe@uni-muenster.de;
c Enamine Ltd, A. Matrosova 23, 01103 Kiev, Ukraine
Fax: +38(044)5373253; e-Mail: nmr@enamine.net;
Further Information

Publication History

Received 5 July 2007
Publication Date:
15 November 2007 (online)

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Abstract

Fluorinated enones were reacted with thiazoles, imidazoles, benzimidazoles and benzthiazoles bearing methylene groups activated by electron-withdrawing substituents. The reactions start with a nucleophilic attack of the methylene carbon on the β-position of the enones. If the starting methylene compound contains a thi­azole ring, pyrones or pyridones were formed due to participation of the ester or nitrile groups. In other cases, imidazo-, benzimidazo- or benzthiazo-pyridines were obtained by participation of the nitrogen atom of the corresponding azole rings. In addition to the final products, some primary products were isolated or proved as intermediates.

Key words

enones - heterocycles - pyridine - 2H-pyran-2-ones - polyfluoroalkyl group