Based on 124-Oxadiazole: Design and Synthesis of a Series of Insensitive Energetic Materials and Discovery of Another Route for the Synthesis of DNAF via Rearrangement

Compounds containing dinitromethyl groups are ideal structural units for energetic materials due to their high density and good oxygen balance. However, these compounds often have drawbacks, such as low decomposition temperatures and high mechanical sensitivity, which limit their practical applications in energetic materials. In order to address these issues, a series of novel nitrogen- and oxygen-rich energetic compounds 7–11 have been successfully designed by incorporating amino groups to enhance hydrogen bonding. Among them, compound 8 exhibited an excellent overall performance (T_dec = 215 °C, ρ = 1.81 g cm^–3, D = 8603 m s^–1, IS > 40 J, FS > 360 N) and displayed good typical secondary explosive characteristics. During the synthesis process, a new and safe method was developed to synthesize 3,4-di(nitramino)furazan and its ion salts. The conversion from 1,2,4-oxadiazole to 1,2,5-oxadiazole via rearrangement was explored through multiple experiments to investigate its mechanism. This new transformation is a valuable complement to the azole–azole rearrangement of the Boulton–Katritzky type.