A simple synthesis of conjugated imine-α-thio- and α-seleno vinylamines

Abstract

The addition of ynamines to N-acyl-S-alkyl(or-aryl)thiobenzimidates and N-acyl-Se-arylselenobenzimidates gives the conjugated acylimine-α-thio-and α-seleno-vinylamines, respectively (together with small amounts of the corresponding amidines); the structure was confirmed by an X-ray structure determination of 1-benzenesulphonyl-4-diethylamino-3-methyl-2-phenyl-4-phenylthio-1-azabutadiene hydrochloride, and a 1,3-sulphur, selenium, or nitrogen shift is proposed to explain formation of these products.