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Nucleophilic trifluoromethylation of R<inf>F</inf>-containing 4-quinolones, 8-aza- and 1-thiochromones with (trifluoromethyl)trimethylsilane

Abstract:

Reactions of N-substituted 2-polyfluoroalkyl-4-quinolones and 8-aza-5,7-dimethyl-2-polyfluoroalkylchromones with (trifluoromethyl) trimethylsilane proceed mainly as a 1,4-nucleophilic trifluoromethylation to give N-substituted 2,2-bis(polyfluoroalkyl)-2,3-dihydroquinolin-4(1H)-ones and 5,7-dimethyl-2,2-bis(polyfluoroalkyl)-2,3-dihydro-4H-pyrano[2,3-b] pyridin-4-ones after acid hydrolysis. Similar reaction with 2-trifluoromethyl- 4H-thiochromen-4-one proceeds as a 1,2-addition to give 2,4-bis(trifluoromethyl) -4H-thiochromen-4-yl trimethylsilyl ether. © 2005 Elsevier B.V. All rights reserved.