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2-Trifluoromethyl-4H-thiochromen-4-one and 2-trifluoromethyl-4H- thiochromene-4-thione: Synthesis and reactivities

Abstract:

2-Trifluoromethyl-4H-thiochromene-4-thione obtained from 2-trifluoromethyl-4H-thiochromen-4-one and P2S5 reacts with aromatic amines, hydrazine hydrate, phenylhydrazine, and hydroxylamine at the C(4) atom of the chromene ring to give the corresponding anils, azine, hydrazones, and oxime of thiochromone. 2-Trifluoromethyl-4H-thiochromen-4-one is oxidized by hydrogen peroxide in AcOH into 4-oxo-2-trifluoromethyl-4H- thiochromene 1,1-dioxide and reduced by NaBH4 to 2-trifluoromethyl- 4H-thiochromen-4-ol or cis-2-(trifluoromethyl)thiochroman-4-ol. When treated with hydrazine hydrate, thiochromen-4-one gives 3(5)-(2-mercaptophenyl)-5(3)- trifluoromethylpyrazole. © 2006 Springer Science+Business Media, Inc.