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* and Jun Yang*
*Hubei Institute of Aerospace Chemotechnology, Xiangyang, Hubei 441003;
SIOC, Chinese Academy of Sciences, Shanghai 200032, PR China,
Email: ppam
tom.com, yangjsioc.ac.cn
H. Huang, Y. Shi, H. Li, H. Li, A. Pang, J. Yang, Org. Lett., 2020, 22, 5866-5869.
DOI: 10.1021/acs.orglett.0c01960
see article for more reactions
Abstract
Potassium 1,1,3,3-tetranitropropane-1,3-diide reacts readily with various (hetero)aryl amines to give the corresponding N-(hetero)aryl-3,5-dinitropyrazoles in good yields.
see article for more examples
Details
The document discusses a one-step method for synthesizing N-(hetero)aryl-3,5-dinitropyrazoles from (hetero)aryl amines using potassium 1,1,3,3-tetranitropropane-1,3-diide (K2TNP). This method offers moderate to excellent yields under mild conditions, completing most reactions in less than 4 hours. The study highlights the significance of pyrazoles in pharmaceuticals, agrochemicals, and materials, noting their inhibitory activities against various biological targets. Traditional methods for synthesizing substituted pyrazoles are complex and inefficient, prompting the development of this new approach. The research also explores the potential of these compounds as energetic materials, emphasizing their high enthalpy of formation, thermal stability, and good sensitivity. The document details the reaction conditions, solvents, and yields for various (hetero)aryl amines, noting that solvent choice significantly impacts reaction speed and yield. The study concludes that this efficient synthesis method could be valuable for drug discovery and developing low-sensitivity, high-stability energetic materials. The document includes experimental procedures, crystallographic data, and detonation performance calculations, with supporting information available online.
Key Words
ID: J54-Y2020
