Synthesis of 2-aryl-2-trifluoromethyl-1,3-thiazolidin-4-ones and 2-aryl-2-trifluoromethyltetrahydro-4H-1,3-thiazin-4-ones and their oxidation with hydrogen peroxide

Abstract

Reactions of aryl trifluoromethyl ketone imines with 2-sulfanylacetic and 3-sulfanylpropanoic acids afforded 2-aryl-2-trifluoromethyl-1,3-thiazolidin-4-ones and 2-aryl-2-trifluoromethyltetrahydro-4H-1,3-thiazin-4-ones, respectively. Their subsequent oxidation with hydrogen peroxide gave the corresponding 2-aryl-2trifluoromethyl-1,3-thiazolidin-4-one 1-oxides and 2-aryl-2-trifluoromethyltetrahydro-4H-1,3-thiazin-4-one 1-oxides and 1,1-dioxides.

Chemistry of 1,3-thiazin-4-ones and their derivatives, 1995 - mid-2018

“…133 Most of the reports used aldehydes, but two of them used ketones. 120,128 T3P 159 has been shown to work with N-acetylcysteine as the thioacid. 93,117,133 Acid catalysis has also been used.…”