Issue 47, 2023

Achieving heat-resistant energetic compounds via silver-catalyzed one-pot cycloaddition of ethyl 2-isocyanoacetate and nitrogen-rich diazonium

Abstract

1,2,4-Triazoles are privileged structural motifs found in many fields, including pharmaceuticals and natural products as well as energetic materials. However, the limited synthetic strategies toward 1,2,4-triazoles have hindered the development of new scaffolds. Herein, we first developed an efficient strategy to construct carboxylate triazoles via a silver oxide catalyzed [3 + 2] cycloaddition reaction of heterocyclic diazonium (2, 3, 4 or 5) with ethyl 2-isocyanoacetate. Compounds 2a–5a were fully characterized and were used to prepare four nitrogen-rich heat-resistant explosives TTTN (2c), BTTN (3c), DTTN (4c) and ATTN (5c). All of the compounds (2c–5c) have high nitrogen contents of >50%. In addition, compound ATTN (5c) shows good performances (D = 8473 m s−1, P = 25.0 GPa, IS > 40 J, and FS > 360 N) and high thermal stability (Td = 318 °C), which suggests its potential as a heat-resistant explosive.

Graphical abstract: Achieving heat-resistant energetic compounds via silver-catalyzed one-pot cycloaddition of ethyl 2-isocyanoacetate and nitrogen-rich diazonium

Supplementary files

Article information

Article type
Paper
Submitted
22 Aug 2023
Accepted
07 Nov 2023
First published
07 Nov 2023

J. Mater. Chem. A, 2023,11, 25992-25999

Achieving heat-resistant energetic compounds via silver-catalyzed one-pot cycloaddition of ethyl 2-isocyanoacetate and nitrogen-rich diazonium

Y. Dong, M. Li, G. Cheng, W. Huang, Y. Liu, C. Xiao and Y. Tang, J. Mater. Chem. A, 2023, 11, 25992 DOI: 10.1039/D3TA05041F

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements