A simple synthetic strategy for the preparation of high nitrogen content azo- and methylene bridged mixed energetic azoles was used. All new compounds were fully characterized by NMR and infrared spectroscopy, elemental analysis, and differential scanning calorimetry (DSC). In addition, the structures of energetic salts 7 and 10 were confirmed by single-crystal X-ray diffraction analysis. Detonation performances, calculated from heats of formation and experimental densities, thermal stabilities, and impact and friction sensitivities suggest possible applications in the field of insensitive energetic materials.