Reaction, Reactivity and Behaviour of α-Chloroacetamides in the Synthesis of Acrylamide Derivatives

Abstract

Abstract In this research, we synthesized unexpected dithiol of ether derivatives (5a-e) by the reaction of α-chloroacetamides (1a-e), carbon disulfide in the presence of sodium isopropoxide in the corresponding alcohol. We expected this reaction to produce 3,6-bis-dimercaptomethylene-1,4-di-substituted-piperazine-2,5-dione (3a-g) in one pot reaction, but, surprisingly, this reaction afforded the dithiol derivatives (5a-e). The structures of the products were elucidated by 1H NMR, 13C NMR, IR, mass spectroscopic data, and elemental analyses. Also, the postulated reaction mechanism provides an explanation of this result and effective the presence of carbon disulfide in the reaction, where the refluxing of compounds (1a-e) in the presence of sodium isopropoxide in the isopropanol afforded piperazine derivatives by intermolecular condensation [1], and then we repeat this reaction by using methoxide, ethoxide, and isopropoxide in the corresponding alcohol we found the same results.