THE SYNTHESIS AND CYCLISATIOM OF THIOACYLATED DIAMINOGUANIDINES

Article abstract of DOI:10.1016/S0040-4020(01)92462-7

The thiobenzoylation of 1,2-diaminoguanidine yields 1-amino-2-thioaroylamidoguanidines which are isolable as their stable hydrazones.They are unaffected by alkalis, but are cyclised by mineral acids, with loss of ammonia, to hydrazones of 2-aryl-5-hydrazino-1,3,4-thiadiazoles, or with elimination of hydrazine, to the appropriate 2-amino-5-aryl-1,3,4-thiadiazoles.The action of acetic anhydride effects the same ring-closures, yielding the corresponding acetylated products. 1,2-Diamino-3-phenylguanidine undergoes a comparable series of reactions.