Reactions of thiazolidine-2,5-dithiones with amino nucleophiles. Synthesis of midazolidine-2,4-dithiones, lmidazo[5,1-a]-imidazole, -pyrimidine, -perimidine, -[2,1-b][1,3,4]thiadiazines and pyrrole-3(2H)-thiones

Abstract

Reactions of 4,4-disubstituted thiazolidine-2,5-dithiones with various amino-containing nucleophiles gave 1-substituted imidazolidine-2,4-dithiones 3 and 11. The diamines, in these reactions, produced fused N-containing heterocycles 7a,b and 10. Imidazo[2,1-b][1,3,4]thiadiazines 14 were synthesized by further reaction of compounds 11 with α-bromoacetophenones. Enamino nitriles reacted as carbanions to give pyrrole-3(2H)-thiones 16.