A Mild and Efficient Synthesis of 3-Aminosubstituted Isothiazole S-Oxides and their 5-Sulfanylsubstituted Derivatives

The present paper describes a mild and efficient method to synthesize 3-aminosubstituted isothiazole sulfoxides taking advantage of arylsulfonyloxaziridines. The reactivity of the resulting isothiazole sulfoxides toward sulfur nucleophiles has been studied and resulted in the formation of 5-sulfanylsubstituted isothiazoles in a fully diastereoselective way. From 3-benzylamino-5-chloro isothiazole S-oxide an addition-elimination reaction took place affording smoothly the corresponding unsaturated 5-sulfanyl derivatives.