Synthesis of dibutadienyl piperazines, 1,1-dithio and 1,4-dithio substituted dienes from nitrodienes

Abstract

Nitrodiene 1a, 1b reacted with 1,4-dithiolbutan and gave the heterocyclic compounds 3a, 3b. 1b gave with 1,3-acetonedithiol the compound 5b. The nitrodiene compound 1b reacted with o-dithiolbenzene (6) and yielded the ketene dithioacetal (7b). Heterocyclic compounds 11a, 11b, 12a, and 12b were prepared from the reactions of 9a with 2,2'-oxydiethanethiol. The compounds 9a, 9b were prepared from 2-nitropentachloro-1,3-butadiene and alkylthiols (8a, 8b). Mono(thio) substituted diene compound 9b gave dibutadienyl piperazine 14b with piperazine in diethylether.