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Pummerer-like Rearrangement Induced Cascade Reactions: Synthesis of Highly Functionalized Imidazoles

Rui Li, Feng Zhou, Xiangdi Huang, Jingfeng Zhao and Hongbin Zhang*

*Yunnan Provincial Center for Research and Development of Natural Products, School of Pharmacy, Yunnan University, Kunming, Yunnan 650091, PR China, Email: zhanghbynu.edu.cn

R. Li, F. Zhou, X. Huang, J. Zhao, H. Zhang, J. Org. Chem., 2023, 88, 739-744.

DOI: 10.1021/acs.joc.2c02411


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Abstract

Pummerer-like rearrangement induced cascade reactions including two carbon-nitrogen bond formations, and concomitant aromatization provide highly substituted imidazoles under mild reaction conditions. The reaction tolerates numerous functional groups and can be used for modifying natural products as well as pharmaceuticals.

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proposed mechanism



Key Words

imidazoles


ID: J42-Y2023