A One-Step Approach to N -(Hetero)aryl-3,5-dinitropyrazoles from (Hetero)aryl Amines

Organic Letters
Haifeng HuangJun Yang

Abstract

Potassium 1,1,3,3-tetranitropropane-1,3-diide (K2TNP) was found to react readily with various (hetero)aryl amines (12 examples) to give corresponding N-(hetero)aryl-3,5-dinitropyrazoles in moderate to excellent yields. The reactions were performed at mild temperature, and most of the reactions completed in less than 4 h. Four potential energetic compounds show high enthalpy of formation, excellent thermal stability, and good sensitivity, with 3-(3,5-dinitropyrazol-1-yl)-1H-1,2,4-triazole (3j) being a potential 2,2',4,4',6,6'-hexanitrostibene (HNS) replacement.

References

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