Tetrahedron p. 1429 - 1436 (1981)
Update date:2022-08-05
Topics:
Kurzer, Frederic
Secker, Jane L.
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.
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Doi:10.1002/anie.200453914
(2004)Doi:10.1021/ja00412a021
(1981)Doi:10.1246/bcsj.75.1367
(2002)Doi:10.1246/cl.1981.283
(1981)Doi:10.1055/s-1981-29521
(1981)Doi:10.1021/jo040216+
(2004)