Citation: Peng Zhao, Zi Zeng, Xiaoming Feng, Xiaohua Liu. Multisubstituted pyrazole synthesis via [3 + 2] cycloaddition/rearrangement/N—H insertion cascade reaction of α-diazoesters and ynones[J]. Chinese Chemical Letters, ;2021, 32(1): 132-135. doi: 10.1016/j.cclet.2020.11.053 shu

Multisubstituted pyrazole synthesis via [3 + 2] cycloaddition/rearrangement/N—H insertion cascade reaction of α-diazoesters and ynones

Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China

xmfeng@scu.edu.cn

liuxh@scu.edu.cn

Received Date: 17 September 2020
Revised Date: 16 November 2020
Accepted Date: 18 November 2020
Available Online: 30 November 2020

Figures(5)

The cascade reactions of alkyl α-diazoesters and ynones using Al(OTf)₃ as the catalyst are described. A series of 4-substituted pyrazoles were obtained via [3 + 2] cycloaddition, 1, 5-ester shift, 1, 3-H shift, and N—H insertion process. Deuterium labelling experiments, kinetic studies and control experiments were carried out for the rationalization of the mechanism.
- Pyrazole,
- Cascade reaction,
- α-Diazoester,
- Ynone,
- Al(OTf)₃
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