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

Haifeng Huang; Yameng Shi; Hui Li; Hongli Li; Aimin Pang; Jun Yang

doi:10.1021/acs.orglett.0c01960

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

Org Lett. 2020 Aug 7;22(15):5866-5869. doi: 10.1021/acs.orglett.0c01960. Epub 2020 Jul 16.

Authors

Haifeng Huang¹, Yameng Shi¹, Hui Li¹, Hongli Li², Aimin Pang³, Jun Yang¹

Affiliations

¹ CAS Key Laboratory of Energy Regulation Materials, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, PR China.
² Biochemistry, College of Medical Technology, Chongqing Medical and Pharmaceutical College, Chongqing 401331, PR China.
³ Science and Technology on Aerospace Chemical Power Laboratory, Hubei Institute of Aerospace Chemotechnology, Xiangyang, Hubei 441003, PR China.

PMID: 32672468
DOI: 10.1021/acs.orglett.0c01960

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.