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

doi:10.6023/cjoc201612029

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (6): 1487-1493.DOI: 10.6023/cjoc201612029 Previous Articles Next Articles

Articles

铜催化偶联反应高效合成苯并[4，5]咪唑并[1，2-b]吡唑衍生物

崔涛, 李丛香, 李明, 文丽荣

青岛科技大学化学与分子工程学院生态化工国家重点实验室培育基地青岛 266042

收稿日期:2016-12-07 修回日期:2017-01-20 发布日期:2017-02-08
通讯作者: 文丽荣 E-mail:wenlirong@qust.edu.cn
基金资助:
国家自然科学基金（Nos.21572110，21372137）和山东省自然科学基金（No.ZR2014BM006）资助项目.

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

Cui Tao, Li Congxiang, Li Ming, Wen Lirong

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

Received:2016-12-07 Revised:2017-01-20 Published:2017-02-08
Contact: 10.6023/cjoc201612029 E-mail:wenlirong@qust.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21572110, 21372137) and the Natural Science Foundation of Shandong Province (No. ZR2014BM006).

1. Efficient Copper-Catalyzed Coupling Reaction for the Synthesis of Benzo[4,5]imidazo[1,2-b]pyrazoles.PDF(4874KB)

Abstract

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.

Key words: copper catalysis, C—N coupling reaction, heterocyclic ketene aminals, benzo[4,5]imidazo[1,2-b]pyrazoles

Cite this article

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]. Chin. J. Org. Chem., 2017, 37(6): 1487-1493.

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铜催化偶联反应高效合成苯并[4，5]咪唑并[1，2-b]吡唑衍生物

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

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