Synthesis, antibacterial and anticancer activity of azo-based and aminomethylene derivatives of cyclic β-keto sulfones.

Herein we describe efficient and cost-effective synthesis of azo-based and aminomethylene derivatives of cyclic β-keto sulfones, specifically, 4,4-disubstituted (E)-2-(2-phenylhydrazineylidene)dihydrothiophen-3(2H)-one 1,1-dioxides and 4,4-disubstituted (E)-2-((methylamino)methylene)dihydrothiophen-3(2H)-one 1,1-dioxides. The azo-based derivatives were prepared through the azo coupling of cyclic β-keto sulfones with aromatic diazonium acetates, in situ prepared by diazotization of appropriate substituted amino benzenes. The aminomethylene derivatives were synthesized through the condensation of cyclic β-keto sulfones with DMF-DMA followed by a transamination reaction with primary amines.