Synthesis of New Antimicrobials. V. Synthesis of Alkylenebis-(thiosemicarbazides) and Their Related Compounds

Several kinds of alkylenebis (thiosemicarbazide) and alkylenebis (bithiourea) derivatives were synthesized in order to examine their antimicrobial activity. 1, 1'-Dibenzylidene-4, 4'-alkylene-bis (thiosemicarbazides) were prepared from 4, 4'-alkylene-bis (thiosemicarbazides) and arylaldehydes, and 1, 1'-diaroyl-4, 4'-hexamethylene-bis (thiosemicarbazides) were prepared by the reaction of 4', 4'-hexamethylene-bis (thiosemicarbazide) with aroyl chlorides. 1, 1'-Dialkyl- or diaryl-6, 6'-alkylene-bis (bithioureas) were synthesized from 4, 4'-alkylene-bis (thiosemicarbazides) and alkyl or aryl isothiocyanates. N, N'-Hexamethylene-bis [2-amino-5-(2-methoxyphenyl) thiadiazole] was prepared by the ring closure of 1, 1'-bis (2-methoxybenzylidene) -4, 4'-hexamethylene-bis (thiosemicarbazide).