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.