Construction of arylthio/arylamino methylene bonds by addition–elimination of nitroolefins with aromatic thiols and amines

Abstract

A highly efficient, catalyst-free, metal-free, atom economical green protocol for the synthesis of arylthio/arylamino methylene compounds by a Michael attack of arylthiols and anilines on nitroolefins derived from acenaphthaquinone and isatin has been developed. The method needs methanol as a reaction solvent and does not require any recrystallization, work-up process or column chromatography. (E)-Arylthio alkenes and (Z)-arylamino alkenes were obtained as the sole products. The results obtained from computational studies using density functional theory on ORCA program (B3LYP/def2-SVP level) are in good agreement with the data obtained from the single crystal X-ray analysis.