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

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

Volume: 5 Issue: 8

Author(s): Alessandro Casoni, Francesca Clerici, Alessandro Contini, Sara Pellegrino and Alessandro Sala

Affiliation:

Keywords: Isothiazoles, oxidation, nucleophilic reactions, S-oxides

Abstract: 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.

Cite this article as:

Casoni Alessandro, Clerici Francesca, Contini Alessandro, Pellegrino Sara and Sala Alessandro, A Mild and Efficient Synthesis of 3-Aminosubstituted Isothiazole S-Oxides and their 5-Sulfanylsubstituted Derivatives, Letters in Organic Chemistry 2008; 5 (8) . https://dx.doi.org/10.2174/157017808786857534