4,5-Dicyano-1,2,3-Triazole-A Promising Precursor for a New Family of Energetic Compounds and Its Nitrogen-Rich Derivatives: Synthesis and Crystal Structures.

Wenli Cao,Jianguo Zhang,Valery P Sinditskii,Jian Qin

doi:10.3390/molecules26216735

Abstract

The nitrogen-rich compounds and intermediates with structure of monocyclic, bicyclic, and fused rings based on 1,2,3-triazole were synthesized and prepared by using a promising precursor named 4,5-dicyano-1,2,3-triazole, which was obtained by the cyclization reaction of diaminomaleonitrile. Their structure and configurational integrity were assessed by Fourier transform-infrared spectroscopy (FT-IR), mass spectrometry (MS), and elemental analysis (EA). Additionally, fourteen compounds were further confirmed by X-ray single crystal diffraction. Meanwhile, the physical properties of four selected compounds (3·H2O, 6·H2O, 10·H2O, and 16) including thermal stability, detonation parameters, and sensitivity were also estimated. All these compounds could be considered to construct more abundant 1,2,3-triazole-based neutral energetic molecules, salts, and complex compounds, which need to continue study in the future in the field of energetic materials.

Highlights

Triazoles (1,2,3-triazole and 1,2,4-triazole) are electron-rich aromatic heterocycles.They accept protons and metal ions so supramolecular systems can be formed by coordinate bond, hydrogen bond, ion-dipole interaction, π-π stacking interaction, hydrophobic interaction, and Van der Waals forces
The synthesis route was described in Scheme 1. 4,5-Dicyano1,2,3-triazole was prepared by one step reaction from diaminomaleodinitrile according to the literature method [26]. 4,5-dicyano-1,2,3-triazole could be hydrolyzed with 1M HCl and 1M acetic acid to obtain 4-carboxamide-5-cyano-1,2,3-triazole (1) in 67% yield
We have shown a study on the 1,2,3-triazole-based compounds and designed five routes to synthesize fifteen compounds starting from commercially available diaminomaleonitrile

Summary

Introduction

Triazoles (1,2,3-triazole and 1,2,4-triazole) are electron-rich aromatic heterocycles. They accept protons and metal ions so supramolecular systems can be formed by coordinate bond, hydrogen bond, ion-dipole interaction, π-π stacking interaction, hydrophobic interaction, and Van der Waals forces. As the synthesis of 1,2,3-triazole can be and efficiently realized via click chemistry, 1,2,3-triazole-based derivatives have aroused growing attention for plenty of studies in recent years. Only few studies of 1,2,3-triazoles derivatives are reported in the field of energetic materials. The research of energetic materials are concentrate on nitrogen-rich heterocyclic compounds which are furazan [6,7,8], 1,2,4-triazole [9,10,11], and tetrazole [12,13,14]

Methods

Results

Conclusion