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Synthesis 2019; 51(04): 874-884
DOI: 10.1055/s-0037-1610661
paper
© Georg Thieme Verlag Stuttgart · New York

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

Dengqi Xue
a   School 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
a   School 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
a   School 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*
a   School of Pharmacy, Fudan University, 826 Zhangheng Road, Zhangjiang Hi-tech Park, Pudong, Shanghai 201203, P. R. of China   Email: limingshao@fudan.edu.cn
b   State Key Laboratory of Medical Neurobiology, Fudan University, 138 Yixueyuan Road, Shanghai 200032, P. R. of China
› Author AffiliationsThe authors thank the National Basic Research Program of China (973 Program, 2015CB931804), the National Natural Science Foundation of China (No. 81473076 and 81673292) and the Science and Technology Commission of Shanghai Municipality (No 15431900100) for financial support.
Further Information

Publication History

Received: 13 August 2018

Accepted after revision: 13 September 2018

Publication Date:
10 October 2018 (online)

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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610661.
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