Three component reaction of aryl diazonium salt with sulfonamide & actonitrile to synthesize N-sulfonyl amidine.

Graphical abstract Highlights • Three-component reaction of aryl diazonium salt with sulfonamide and acetonitrile. • Nitrilium ion intermediate generates in reaction of aryldiazonium salt with nitrile. • Trapping nitrilium ion by sulfonamide to give N -sulfonyl amidine. • Trapping nitrilium ion by indole to give indolyl imine. Abstract A new method was developed to prepare N -sulfonyl amidine compounds through three-component reaction of aryl diazonium salts with sulfonamides and acetonitrile, in which, nitrilium ion intermediate, generated from the reaction of aryldiazonium salt with nitrile, was subsequently trapped by sulfonamides. A series of N -sulfonyl amidine derivatives were synthesized by using various types of aryl diazonium salts, sulfonamides and nitriles. In addition, indolyl imine products could also be prepared by using indole as the nucleophile to trap nitrilium ion intermediate. [ABSTRACT FROM AUTHOR]