Synthesis of 1,3-Selenazol-2(3H)-imines

Abstract

The reaction of N,N’-diarylselenoureas 16 with phenacyl bromide in EtOH under reflux, followed by treatment with NH3 , gave N,3-diaryl-4-phenyl-1,3-selenazol-2(3H)-imines 13 in high yields (Scheme 2). A reaction mechanism via formation of the corresponding Se-(benzoylmethyl)isoselenoureas 18 and subsequent cyclocondensation is proposed (Scheme 3). The N,N’-diarylselenoureas 16 were conveniently prepared by the reaction of aryl isoselenocyanates 15 with 4-substituted anilines. The structures of 13a and 13c were established by X-ray crystallography.