New heterocyclic compounds from reactions of mono(aryl-and-alkythio)-substituted 2-nitrotetrachlorobutadienes and 2-nitrohalobutadiene with cystamine and dithiols

Abstract

Mono(thio)substituted 2-nitro-tetrachloro-1,3-butadiene (1) gives 3a, b, 4a-b and 5a-b by the reaction with 2-mercaptoethylaminehydrochloride in EtOH containing sodium hydroxide. Heterocyclic thioether 9 was obtained from reaction of 2-nitropentachlorobutadiene (7) with 1,3-dithioacetone (8). Ketene dithioacetal 11 is prepared by reacting 2-nitropentachloroburadiene (7) with o-dithio-phenole (10). Mono(4-chlorophenylthio)-2-nitro-1,3-butadiene (12) in water-ethanol mixture in the presence of sodium hydroxide reacted with dithiols 13a-b to give cyclic thioethers 14a-b and linear chain thioethers 15a-b.