Nucleophilic Catalyzed Structural Binary Cleavage of a Fused [5,5]-Bicyclic Compound

Org Lett. 2021 Dec 17;23(24):9408-9412. doi: 10.1021/acs.orglett.1c03534. Epub 2021 Nov 30.

Abstract

Structural binary cleavage of 3,7-diamino-2,6-dinitro-1H,5H-pyrazolo-[1,2-a]pyrazole-1,5-dione 3, under nucleophilic conditions, leads to the formation of a monocyclic pyrazole unit of 5-amino-4-nitro-1,2-dihydro-3H-pyrazol-3-one, 4. Additionally, various salts of the pyrazole ring were synthesized and fully characterized. Detonation properties and mechanical sensitivities of 4 and other new compounds are remarkably improved compared to 3. This simple and efficient strategy is highly desirable for future studies on the development of insensitive and high performing materials.