New N-, S-substituted nitrodienes from reactions of primary and secondary amines with mono(thio) substituted nitrodienes

Abstract

N, S-substituted butadiene compounds 3a-e have been obtained from mono(thio)substituted 2-nitrodiene compounds la-e with morpholine in ether. Compounds 1b-e give 7b-e by the reaction with 4-methylpiperazine in ether. Mono(thio)substituted diene compounds 1b-e react with 1-(2-hydroxyethyl)piperazine (8) in ether yielding compounds 9b-c. Dibutadienyl substituted compounds 5b and 5c are prepared by mixing 2 moles of mono(thio)substituted 2-nitrobutadienes 1b-c with 1 mole piperazine (4). S-substituted nitrodiene compounds 1d-e give 12d and 12e by the reaction with piperazine in ether.