Synthesis of 3-N-Phenylthiocarbamoyl-2-butenamides from 4-Benzoyl-5-phenylamino-2,3-dihydrothiophene-2,3-dione in Aqueous Medium at Room Temperature

摘要

Background: Earlier we found that the reaction of 4-benzoyl-5-phenylamino-2,3-dihydrothiophene-2,3-dione (1) with primary aromatic amines, secondary aliphatic amines and N,N '-dinucleophiles such as 1-aminoguanidine, guanidine, urea, and 1,2-phenylenediamine in ethanol or acetic acid at high temperature gave the substituted thiophenes, amide and heterocyclic derivatives that have N-phenylthiocarbamoyl group, respectively. As a part of our studies on the intermediate 1 in relation to the synthesis of thioamides in aqueous medium, we now report the reactions of 1 with amines at room temperature in the THF-H2O (1:1) system. The reaction of 1 with primary and secondary aliphatic amines, N, N '-dinucleophiles such as hydrazine and guanidine and tertiary aromatic and aliphatic amines led to 3-N-phenylthiocarbamoyl-2-butenamides 2a-n.