Abstract

1,3-thiazolidin-4-ones, also known as thiazolidin-4-ones, are known to have a very wide range of biological activity. The corresponding S-oxides may show enhanced activity, and therefore viable synthetic routes to these S-oxides are required. S-oxidation of 3-cyclohexyl-2-phenyl-1,3-thiazolidin-4-ones with Oxone^® was investigated. For all compounds evaluated, selective oxidation to the sulfoxide was realized using 3 equivalents of Oxone^® at room temperature. Alternatively, the sulfone was prepared selectively at high temperature by increasing the equivalents of Oxone^® used; the extent of this selectivity was affected by the substituent of the aromatic ring. In those cases in which the reaction produced a mixture of the sulfoxide and sulfone, the ratio of the products was quantified by ¹H NMR.

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