4‐(1‐Amino‐5‐aminotetrazolyl)methyleneimino‐3‐methylfuroxan and Its Derivatives: Synthesis, Characterization, and Energetic Properties

The condensation reaction of 4‐formyl‐3‐methylfuroxan with 1,5‐diaminotetrazole led to 4‐(1‐amino‐5‐aminotetrazolyl)methyleneimino‐3‐methylfuroxan (1) in high yield. Its structure was confirmed by an X‐ray diffraction study. 4‐(1‐Amino‐5‐nitriminotetrazolyl)methyleneimino‐3‐methylfuroxan (2) was obtained through the nitration of 1 with 100 % HNO3. The nitrogen‐rich salts of 2 with bases such as 1‐amino‐1,2,3‐triazole (3), 4‐amino‐1,2,4‐triazole (4), and 3‐amino‐1,2,4‐triazole (5) were synthesized and characterized by IR, Raman, and NMR spectroscopy and elemental analysis. In addition, the structures of 2, 4, and 5 were further confirmed by single‐crystal X‐ray diffraction analyses. Compound 5 decomposes at 183 °C, whereas 3 and 4 are less stable and decompose at 139 and 164 °C, respectively. The heats of formation, detonation parameters, and impact sensitivity of 1–5 were investigated by theoretical and experimental methods.