Synthesis of 5,7-diamino1,2,4 triazolo[1,2-a1,3,5 triazines via annulation of 1,3,5-triazine ring onto 3(5)-amino-1,2,4-triazoles

Abstract

The 5,7-diamino[1,2,4]triazoeo[1,5-a][1,3,5]triazines were synthesized by cyclocondensation of 3(5)-amino-1,2,4-triazoles with cyanoguanidine. The substituted 3(5)-amino-1,2,4-triazoles were prepared from corresponding hydrazides and S-methylisothiourea via ring closure of the intermediate acylaminoguanidines. The 3,5-diamino-1,2,4-triazoles were prepared using partial aminolysis of dimethyl N-cyanodithiocarbonimidate followed by cyclization of the obtained N-substituted N′-cyano-S-methylisothioureas with hydrazine. The structures of the prepared compound were confirmed using NMR spectral data. © 2007 The Japan Institute of Heterocyclic Chemistry.