Citation: Cui Tao, Li Congxiang, Li Ming, Wen Lirong. Efficient Copper-Catalyzed Coupling Reaction for the Synthesis of Benzo[4, 5]imidazo[1, 2-b]pyrazoles[J]. Chinese Journal of Organic Chemistry, ;2017, 37(6): 1487-1493. doi: 10.6023/cjoc201612029 shu

Efficient Copper-Catalyzed Coupling Reaction for the Synthesis of Benzo[4, 5]imidazo[1, 2-b]pyrazoles

State Key Laboratory Base of Eco-chemical Engineering, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042

Corresponding author: Wen Lirong, wenlirong@qust.edu.cn
Received Date: 7 December 2016
Revised Date: 20 January 2017

Fund Project: the National Natural Science Foundation of China 21572110the Natural Science Foundation of Shandong Province ZR2014BM006the National Natural Science Foundation of China 21372137

Figures(4)

A fast and efficient CuI-catalyzed intramolecular C—N coupling reaction of N-(2-bromoaryl)-1H-pyrazol-5-amines to synthesize benzo[4, 5]imidazo[1, 2-b]pyrazoles has been developed from N-(2-bromoaryl)-thioacetanilides. A series of benzo[4, 5]imidazo[1, 2-b]pyrazoles were obtained in excellent yields with CuI/heterocyclic ketene aminals catalytic system in the presence of Cs₂CO₃ in dimethyl sulfoxide (DMSO) at 120 ℃ within 10 min. The reaction provides an fast and efficient protocol to access a series of benzo[4, 5]imidazo[1, 2-b]pyrazoles in good to high yields.
- copper catalysis,
- C—N coupling reaction,
- heterocyclic ketene aminals,
- benzo[4, 5]imidazo[1, 2-b]pyrazoles
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