Репост из: Organic Letters ASAP
Synthesis of Azido Energetic Compounds Based on 2-(Pyrazol-4-yl)pyrazolo[4,3-e][1,2,4]triazolo[1,5-c][1,2,3]triazine via an Atom-Economical Intramolecular Dutt–Wormall-Type Process
Yiling Yang, Xu Yang, Hao Guo, Yi Wang, Jiaqi Chen, Qinglan Li, Xin Li, Wenjin Zhang*, He Huang*, Chenghui Sun*
Abstract: Azido energetic compounds are important components of primary explosives because of their excellent initiating ability. However, azido-group installation in energetic molecules usually relies on hazardous reagents such as NaN3. Herein, we report an atom-economical azido-group installation strategy based on an intramolecular Dutt-Wormall-type process that requires neither an external azide reagent nor an additional amine source. Using this approach, azido-containing energetic compound ATPTT was synthesized, showing excellent detonation performance (Dv = 9217 m/s) together with acceptable thermal stability (147 °C) and sensitivity (IS = 3.5 J; FS = 40 N). This work offers a new route to azido-functionalized nitrogen-rich energetic heterocycles and highlights its value for the development of high-performance primary explosives.
❯ Link to the article
Yiling Yang, Xu Yang, Hao Guo, Yi Wang, Jiaqi Chen, Qinglan Li, Xin Li, Wenjin Zhang*, He Huang*, Chenghui Sun*
Abstract: Azido energetic compounds are important components of primary explosives because of their excellent initiating ability. However, azido-group installation in energetic molecules usually relies on hazardous reagents such as NaN3. Herein, we report an atom-economical azido-group installation strategy based on an intramolecular Dutt-Wormall-type process that requires neither an external azide reagent nor an additional amine source. Using this approach, azido-containing energetic compound ATPTT was synthesized, showing excellent detonation performance (Dv = 9217 m/s) together with acceptable thermal stability (147 °C) and sensitivity (IS = 3.5 J; FS = 40 N). This work offers a new route to azido-functionalized nitrogen-rich energetic heterocycles and highlights its value for the development of high-performance primary explosives.
❯ Link to the article