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Updated: Jun 28, 2026

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Nitration of Tricyclic Compound Bis([1,2,4]triazole)[1,5-b:3',4'-f]pyridazin-8-amine: Mechanistic Insights and
Benyue Guo1, Xinbo Yang1,2, Xinyuan Zhao1
1School of Materials Science & Engineering, Beijing Institute of Technology, Beijing 100081, China.
Abstract:
The nitration reaction plays a pivotal role in the construction and synthesis of energetic compounds. A new [5,6,5]-tricyclic compound bis([1,2,4]triazole)[1,5-b:3',4'-f]pyridazin-8-amine (4) was synthesized, and its nitration reaction was investigated thoroughly. The nitrated products 5·H2O, 6, 8, and 9 and rearrangement products 7 were obtained by nitration screening performed across a range of temperature gradients (0-100 °C), acid concentrations (HNO3 = 40% to 100%), nitration systems (HNO3 and HNO3/H2SO4), and reaction durations (1 h-12 h). A new methodology for azasydnone synthesis is established by the synthesis of 7. The nitration and rearrangement reaction mechanism was fully studied by quantum chemical calculations. Compound 9 has good thermal stability (Tdec = 222 °C), high detonation properties (v = 8554 m·s-1), and insensitivity (IS > 40 J; FS > 360 N). These findings provide deep mechanistic insights while broadening the synthetic landscape of fused-ring nitration.
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