Citation: Li Fuwei, Wang Xiaolong, Yu Haitao. Preparation of 1,3,5-Trisubstituted Pyrazoles with Cascade Reaction Catalyzed by Cu between Hydrazonoyl Halide and Terminal Alkynes[J]. Chinese Journal of Organic Chemistry, ;2016, 36(5): 1127-1132. doi: 10.6023/cjoc201511033 shu

Preparation of 1,3,5-Trisubstituted Pyrazoles with Cascade Reaction Catalyzed by Cu between Hydrazonoyl Halide and Terminal Alkynes

1.
Nanjing University of Chinese Medicine, School of Pharmacy, Nanjing 210023

Corresponding author: Yu Haitao, njubilly@foxmail.com
Received Date: 18 November 2015
Revised Date: 22 December 2015

Fund Project: Project supported by the National Natural Science Foundation of China No. 81302650

Figures(2)

Cascade reaction, including nucleophilic substitution and addition cyclization, catalyzed by Cu⁺ salt between substituted aryl hydrazonoyl halides and terminal alkynes could produce 1,3,5-trisubstituted pyrazoles. The method employed easily available aryl hydrazonoyl halide and terminal alkynes as starting materials under 45 ℃ in green acetonitrile/water solvent, regioselectively generating 1,3,5-trisubstituted pyrazoles in high yield. Above all, functional groups containing active hydrogen would not disturb this reaction, example for carboxyl and hydroxyl. In this work 17 pyrazole derivatives with different substituent group were achieved by this method. So it could be a general method to synthesize 1,3,5-trisubstituted pyrazoles.
- 1,3,5-trisubstituted pyrazole,
- hydrazonoyl halide,
- terminal alkyne,
- Cascade reaction
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沈阳化工大学材料科学与工程学院沈阳 110142