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Updated: Oct 1, 2025

Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
Published on: February 9, 2021
From Nitro- to Heterocycle-Functionalized 1,2,4-Triazol-3-one Derivatives: Achieving High-Performance Insensitive
Yuji Liu1, Zhiwei Zeng1, Wei Huang1
1School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, China.
Abstract:
5-Nitro-1,2,4-triazol-3-one, a nitro-functionalized 1,2,4-triazol-3-one (TO) derivative, shows excellent energetic properties and promising application potential. However, the use of the TO skeleton as an energetic material is still largely underexplored both theoretically and practically. We report here a mild and efficient method for obtaining the TO skeleton via a reaction of aminocarbohydrazide with BrCN. Two energetic compounds (2 and 5) were synthesized and fully characterized by 15N nuclear magnetic resonance, two-dimensional 1H-15N heteronuclear multiple-bond correlation, and single-crystal X-ray diffraction. The reaction mechanism was also studied with the aid of quantum calculations. Compound 2 shows promising properties as a high-performance insensitive energetic material.
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