78968-44-2Relevant academic research and scientific papers
Synthesis, oxidation and dehydrogenation of cyclic N,O- and N,S-acetals. Part 1. Transformation of N,S-acetals: 3-acyl-1,3,4-thiadiazolines
Somogyi, Laszlo
, p. 2243 - 2267 (2007/10/03)
Aldehyde and ketone thiosemicarbazones are synthesized and cyclized into 3-acyl-1,3,4-thiadiazolines under acylating conditions. Reactions of the 2-monosubstituted heterocycles with oxidizing and dehydrogenating agents (KMnO4 or for the first time with CAN, DDQ, IBDA) lead to the formation of thiadiazoles. CAN oxidation of 2,2-disubstituted 3-acyl-1,3,4-thiadiazolines regenerates the parent ketones efficiently.
THE SYNTHESIS AND CYCLISATIOM OF THIOACYLATED DIAMINOGUANIDINES
Kurzer, Frederic,Secker, Jane L.
, p. 1429 - 1436 (2007/10/02)
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.
