TY - JOUR
AU - Hanks, David R.
AB - Ethoxycarbonylhydrazine reacts with two molar proportions of diphenylcarbodi-imide to give the 2 : 1-adduct 1,2-bis-′-diphenylamidino-1-ethoxycarbonylhydrazine. This cyclises, with loss of arylamine, to 1-ethoxycarbonyl-4-phenyl-3,5-bisphenylimino-1,2,4-triazolidine, which can be hydrolysed to give 3,5-dianilino-4-phenyl-1,2,4-triazole. The 2 : 1-adduct is hydrolysed by ethanolic hydrochloric acid to 1-carboxy-1,2-bis-′-diphenylamidinohydrazine, which can be cyclised by alkali to give 3-anilino-5-hydroxy-4-phenyl-1,2,4-triazole.Use of di--tolyl- or di--bromophenylcarbodi-imide results in di-addition and simultaneous loss of ethanol to afford 4-aryl-2-′-diarylamidino-5-arylimino-1,2,4-triazolidin-3-ones; these are cleaved to give 4-aryl-3-arylamino-5-hydroxy-1,2,4-triazoles and diarylureas by alkaline hydrolysis. The addition of the carbodi-imide to ethoxycarbonylhydrazine may be performed in two distinct stages with the same results; the intermediate 1-′-diarylamidino-2-ethoxycarbonylhydrazine is isolable and a route is thus provided to -triazolidinones containing two different aryl substituents.
TI - Heterocyclic compounds from urea derivatives. Part XIII. Addition–cyclisations of ethoxycarbonylhydrazine and carbodi-imides
JF - Journal of the Chemical Society C Organic
DO - 10.1039/j39680001375
DA - 1968-01-01
UR - https://www.deepdyve.com/lp/royal-society-of-chemistry/heterocyclic-compounds-from-urea-derivatives-part-xiii-addition-oHyrq84btD
SP - 1375
EP - 1380
DP - DeepDyve
ER -