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

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.

Tolmachova N. A.; Gerus I. I.; Vdovenko S. I.; Haufe G.; Kirzhner Y. A.
Synthesis 2007, 24, 3797-3806
DOI: 10.1055/s-2007-990891