A new conjugated tripoid N4 system containing furazan and triazolofurazan cores linked by a nitrogen bridge

Two thermostable representatives of methyl-substituted triazolofurazan derivatives with zwitterionic N⁺–N^– bonds were obtained via the thermal cyclization of N,N’-bis(azidofurazanyl)-N-methyltriazene. 5-(N-Azidofurazanyl-N-methylamino)triazolofurazan was the product of known intramolecular reaction of neighboring azido and azo groups. Its isomer with methyl group in the triazolofurazan core was formed in the course of new cyclization of azido and triazene groups representing an original N–N bond formation reaction giving an unusual zwitterionic heterocyclic system.