Una nuova classe di isotiazoli : sintesi e reattività di 3-amminoisotiazol S-ossidi

In this work we described i) the synthesis of chiral racemic isothiazole S-oxides, starting from the corresponding 3-aminosubstituted isothiazoles; a mild and efficient method to synthesize chiral 3-aminosubstituted isothiazole sulfoxides taking advantage of (+) and (-)((8,8-dichlorocamphoryl)sulfonyl)oxaziridine. The determination of the absolute configuration of the chiral sulfoxide was achieved by theoretical calculation of CD spectra. The reason for the observed stereoselectivity was enlightened by means of analysis of thedata using DFT calculations ii)studies on their reactivity toward nucleophiles with the aim to demonstrate the ability of the sulfoxide group to direct the addition iii)studies on the efficacy of this system as an effective reaction partner in cycloaddition reactions which would allow the preparation of anellated isothiazole S-oxide derivatives of both chemical and pharmacological interest. The exploitation of the sulfoxide system could be considered of large interest due to the significant stereodifferentiating ability of the sulfinyl function. Moreover, taking into account the general interest toward environmental contamination, in this work efforts were devoted to develop the process with reduced environmental impact.