Fused rings with N-oxide and -NH: good combination for high density and low sensitivity energetic materials.

Oxidation reactions of 3,6-diamino-1,2,4-triazolo[4,3-b][1,2,4,5]tetrazine give four N-oxide compounds. Because of the presence of an amino group and the N-oxide moiety, these compounds are extensively hydrogen bonded. Resulting from π-π stacking interactions between the fused rings, compounds 1-3 are impact and friction insensitive, are thermally stable and have good density.