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Synthesis 2007(24): 3797-3806
DOI: 10.1055/s-2007-990891
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
Weitere Informationen
Received
5 July 2007
Publikationsdatum:
15. November 2007 (online)
Publikationsverlauf
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.
Key words
enones - heterocycles - pyridine - 2H-pyran-2-ones - polyfluoroalkyl group
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