Synthesis of Energetic 7-Nitro-3,5-dihydro-4H-pyrazolo[4,3-d][1,2,3]triazin-4-one Based on a Novel Hofmann-Type Rearrangement |
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Authors: | Fu-Qiang Bi Yi-Fen Luo Jun-Lin Zhang Huan Huo Bo-Zhou Wang |
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Affiliation: | 1.Xi’an Modern Chemistry Research Institute, Xi’an 710065, China; (F.-Q.B.); (Y.-F.L.); (H.H.);2.College of Chemistry & Materials Science, Northwest University, Xi’an 710127, China |
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Abstract: | Rearrangement reactions are efficient strategies in organic synthesis and contribute enormously to the development of energetic materials. Here, we report on the preparation of a fused energetic structure of 7-nitro-3,5-dihydro-4H-pyrazolo[4,3-d][1,2,3]triazin-4-one (NPTO) based on a novel Hofmann-type rearrangement. The 1,2,3-triazine unit was introduced into the fused bicyclic skeleton from a pyrazole unit for the first time. The new compound of NPTO was fully characterized using multinuclear NMR and IR spectroscopy, elemental analysis as well as X-ray diffraction studies. The thermal behaviors and detonation properties of NPTO were investigated through a differential scanning calorimetry (DSC-TG) approach and EXPLO5 program-based calculations, respectively. The calculation results showed similar detonation performances between NPTO and the energetic materials of DNPP and ANPP, indicating that NPTO has a good application perspective in insensitive explosives and propellants. |
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Keywords: | synthesis NPTO Hofmann-type rearrangement mechanism crystal |
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