Transformation of O-Amidinylhydroxylamine into Benzothiazoles via Iminocarbonyl Sulfenamides

摘要

The reaction of O-amidinylhydroxylamine 3 with aryl isothiocyanates leads to the formation of benzothiazole derivatives 5a-c.The proposed mechanism of the reaction involves initial formation of iminocarbonyl sulfenamides A which,in turn,undergo spontaneous sulfurization of aromatic ring with loss of amine 7.The later compound reacts with excess aryl isothiocyanate to give l,3-diazaspiro[4,5]decane-2-thione 6.