Metal-Free Radical Cyclization of Vinyl Isocyanides with Alkanes: Synthesis of 1-Alkylisoquinolines

Dengqi Xue; Yijie Xue; Haihua Yu; Liming Shao

doi:10.1055/s-0037-1610661

Synthesis, Table of Contents

Synthesis 2019; 51(04): 874-884
DOI: 10.1055/s-0037-1610661

paper

Metal-Free Radical Cyclization of Vinyl Isocyanides with Alkanes: Synthesis of 1-Alkylisoquinolines

Dengqi Xue

^aSchool of Pharmacy, Fudan University, 826 Zhangheng Road, Zhangjiang Hi-tech Park, Pudong, Shanghai 201203, P. R. of China Email: limingshao@fudan.edu.cn

,

Yijie Xue

^aSchool of Pharmacy, Fudan University, 826 Zhangheng Road, Zhangjiang Hi-tech Park, Pudong, Shanghai 201203, P. R. of China Email: limingshao@fudan.edu.cn

,

Haihua Yu

^aSchool of Pharmacy, Fudan University, 826 Zhangheng Road, Zhangjiang Hi-tech Park, Pudong, Shanghai 201203, P. R. of China Email: limingshao@fudan.edu.cn

,

Liming Shao*

^aSchool of Pharmacy, Fudan University, 826 Zhangheng Road, Zhangjiang Hi-tech Park, Pudong, Shanghai 201203, P. R. of China Email: limingshao@fudan.edu.cn

^bState Key Laboratory of Medical Neurobiology, Fudan University, 138 Yixueyuan Road, Shanghai 200032, P. R. of China

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Abstract

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Abstract

A metal-free radical cyclization reaction of vinyl isocyanides with alkanes is developed, allowing convenient access to a diverse range of potentially valuable 1-alkylisoquinolines. The methodology is simple and efficient, demonstrating excellent functional group tolerance and broad substrate scope. A mechanism involving a radical process is supported by kinetic isotope effect and radical inhibition studies.

Key words

metal-free - radical cyclization reaction - vinyl isocyanides - alkanes - 1-alkylisoquinolines

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References

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