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

doi:10.1021/acs.orglett.6c02547

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^*

^*Corresponding author for this work

Beijing Institute of Technology
Qingyang Chemical Industry Corporation

Research output: Contribution to journal › Letter › peer-review

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 (D_v = 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.

Original language	English
Pages (from-to)	9065-9070
Number of pages	6
Journal	Organic Letters
Volume	28
Issue number	28
DOIs	https://doi.org/10.1021/acs.orglett.6c02547
Publication status	Published - 17 Jul 2026
Externally published	Yes

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@article{44b0fdabee8a4931a4fa3b8037f107a6,

title = "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",

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.",

author = "Yiling Yang and Xu Yang and Hao Guo and Yi Wang and Jiaqi Chen and Qinglan Li and Xin Li and Wenjin Zhang and He Huang and Chenghui Sun",

note = "Publisher Copyright: {\textcopyright} 2026 American Chemical Society",

year = "2026",

month = jul,

day = "17",

doi = "10.1021/acs.orglett.6c02547",

language = "English",

volume = "28",

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journal = "Organic Letters",

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Yang, Y, Yang, X, Guo, H, Wang, Y, Chen, J, Li, Q, Li, X, Zhang, W, Huang, H & Sun, C 2026, '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', Organic Letters, vol. 28, no. 28, pp. 9065-9070. https://doi.org/10.1021/acs.orglett.6c02547

TY - JOUR

T1 - 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

AU - Yang, Yiling

AU - Yang, Xu

AU - Guo, Hao

AU - Wang, Yi

AU - Chen, Jiaqi

AU - Li, Qinglan

AU - Li, Xin

AU - Zhang, Wenjin

AU - Huang, He

AU - Sun, Chenghui

PY - 2026/7/17

Y1 - 2026/7/17

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/105044811128

U2 - 10.1021/acs.orglett.6c02547

DO - 10.1021/acs.orglett.6c02547

M3 - Letter

AN - SCOPUS:105044811128

SN - 1523-7060

VL - 28

SP - 9065

EP - 9070

JO - Organic Letters

JF - Organic Letters

IS - 28

ER -

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

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