Reactions of methyl 4-aminofurazan-3-carboximidate with nitrogen-containing nucleophiles

Methyl 4-aminofurazan-3-carboximidate reacts with aromatic amines and hydrazines to give the corresponding amidines and amidrazones. The reaction of the title compound with o-phenylenediamine yields 3-amino-4-(2-benzimidazolyl)furazan, and with acylhydrazines N-2-acyl-4-aminofurazan-3-carbohydrazides are formed. The latter undergo thermal intramolecular cyclization with formation of 3-amino-4-(1,2,4-triazol-3-yl)furazan derivatives containing various substituents in position 5 of the triazole ring.