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;
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Publikationsverlauf

Received 5 July 2007
Publikationsdatum:
15. November 2007 (online)

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.