Selective Synthesis of Ortho-Substituted 2-Aryl-3-phenyl-1,3-thiazolidin-4-one Sulfoxides and Sulfones by S-Oxidation with Oxone®

Kevin C. Cannon, Alaa Alkurdi, Humayra Himel, Iryna Kurochka, Sabrina Liu, Miguel Costa, Brynn Sundberg, Anthony F. Lagalante


S-oxidation of 2-aryl-3-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. Attempts to selectively prepare the sulfones of ortho-substituted 2-aryl-3-phenyl-1,3-thiazolidin-4-ones at high temperature by increasing the equivalents of Oxone® used were typically unsuccessful. These results contrast significantly with ortho-substituted 2-aryl-3-cyclohexyl-1,3-thiazolidin-4-ones evaluated previously. The extent of this selectivity was affected by the substituent and its position on the C2 aromatic ring. The ratio of the sulfoxide and sulfone products was quantified by isolating the products by liquid chromatography.

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International Journal of Chemistry   ISSN 1916-9698 (Print)   ISSN 1916-9701 (Online)

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