A Novel Synthesis of Highly Functionalized 1,2,4-Diselenazolidines from Acyl Isoselenocyanates

Abstract

A simple one-pot synthesis of highly functionalized 1,2,4-diselenazolidines is described. Treatment of an acyl chloride with potassium selenocyanate in acetone gave an acyl isoselenocyanate and propane-2-selone, which both reacted with benzylamine or its derivatives to give the required products.

Synthesis, Reactivity and Antimicrobial Activity of a Series of 2-Arylamino-1,3-selenazoles

“…The formation of the 1,2,4-diselenazolidine may be explained by two sequential nucleophilic additions of aniline to PhNCSe, followed by oxidation of the intermediate. This mechanism is consistent with that proposed by Yavari for the formation of functionalized 1,2,4-diselenazolidenes from acyl isoselenocyanates [24]. A structurally similar diselenazole was isolated by Woollins as an unexpected During one preparation of PhNCSe (1a) we isolated a small amount of material, which was not the expected product as evident from its proton NMR spectrum.…”