Ionic liquids as unique solvents in one-pot synthesis of 4-(n,2,2,2-tetranitroethylamino)-3-R-furazans.

An efficient two-step one-pot protocol for the synthesis of N-nitrated trinitroethylamino furazans in an ionic liquid has been developed involving the condensation of aminofurazans with trinitroethanol and the N-nitration of an intermediate Mannich base. Trinitroethylnitramino derivatives have been synthesized and characterized by multinuclear NMR spectroscopy and X-ray crystallography. A role of the N,2,2,2-tetranitroethylamino group for stabilization of the high-density crystal-packing motif is described. The performance calculations gave detonation pressures and velocities for the furazan derivatives in a range of about 31-36 GPa and 8330-8745 ms(-1), respectively, which makes them competitive energetic materials. Furthermore, due to the positive oxygen balance, the compounds could be potential oxidizers for energetic formulations.