3-Nitro, 1-Amino Guanidine and 5-Hydrazino-1H-Tetrazole Derivatives as New Energetic Materials

The synthesis of 3-amino-1-nitroguanidine (3-anq) and 5-hydrazino tetrazole (5-ht) derivatives as new energetic materials are described. reaction of 3-anq with triethyl orthoformate leads to the formation of 3-nitramino triazole while no reaction was observed whit 5-ht. addition of nan3 to a mixture of 3-anq and triethyl orthoformate, afforded 1-nitroguanidyl tetrazole in excellent yield. on the other hand, these compounds showed different reactivity toward dicyandiamide. cyclization of 5-ht with dicyandiamide in etoh/water reflux caused formation of 3,5-diamino-1-(1h-tetrazol-5-yl)-1h-1,2,4-triazole in good yield, nitration of which afforded 3,5-dinitramino-1-(1h-tetrazol-5-yl)-1h-1,2,4-triazole as a potentially new high energetic molecule. no reaction was observed between 3-anq and dicyandiamide. the reaction of 3-anq and 5-ht were exanimated with trichloro triazine (tct). 5-ht gave mixture of products while no reaction between 3-anq and tct was detected. unusual hydrazone condensation was observed between 3-anq and acetone, when acetone/water mixture used as solvent at 0 °c.