Cu(i) catalysed annulation of isothiocyanates/isocyanates with 2-iodo-sulfonamides: synthesis of benzodithiazines, benzothiadiazinones, benzothiazinylidene-anilines and benzothiazolylidene-anilines.

ABSTRACT

An efficient Cu(i)-catalysed cyclisation reaction of 2-iodobenzene sulfonamides with aryl-isothiocyanates and isocyanates that affords functionalised benzodithiazines and benzothiadiazinones, respectively, has been developed. Thus, in the reaction with aryl isothiocyanates (Ar-N[double bond, length as m-dash]C[double bond, length as m-dash]S), the C[double bond, length as m-dash]S moiety participates in the cyclisation leading to a dithiazine. By contrast, in the case of aryl isocyanates (Ar-N[double bond, length as m-dash]C[double bond, length as m-dash]O), the N[double bond, length as m-dash]C part is involved in the cyclisation and a thiadiazinone is obtained. Analogous reactions of isothiocyanates with N-tosyl-2-iodo-anilines and 2-iodo-benzyl sulfonamides afford (benzothiazin-2-ylidene)anilines and (benzothiazol-2-ylidene)anilines, respectively. Probable mechanistic pathways are briefly discussed.