Radical-Triggered Tandem Reaction of Vinyl Azides with Isopropylxanthic Disulfide for the Synthesis of 6-Sulfanylmethyl Phenanthridines

doi:10.6023/cjoc201807025

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (2): 515-520.DOI: 10.6023/cjoc201807025 Previous Articles Next Articles

Notes

烯基叠氮与二异丙基黄原酸酯的自由基串联反应:合成6-巯甲基菲啶

陆露露, 周丙伟, 金红卫, 刘运奎

浙江工业大学化学工程学院绿色化学与技术国家重点实验室培育基地杭州 310014

收稿日期:2018-07-16 修回日期:2018-09-10 发布日期:2018-10-12
通讯作者: 金红卫, 刘运奎 E-mail:jhwei828@zjut.edu.cn;ykuiliu@zjut.edu.cn
基金资助:
国家自然科学基金（Nos.21772176，21372201）、浙江工业大学"省重中之重一级学科"开放基金资助项目.

Radical-Triggered Tandem Reaction of Vinyl Azides with Isopropylxanthic Disulfide for the Synthesis of 6-Sulfanylmethyl Phenanthridines

Lu Lulu, Zhou Bingwei, Jin Hongwei, Liu Yunkui

State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014

Received:2018-07-16 Revised:2018-09-10 Published:2018-10-12
Contact: 10.6023/cjoc201807025 E-mail:jhwei828@zjut.edu.cn;ykuiliu@zjut.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21772176, 21372201), the Opening Foundation of Zhejiang Key Course of Chemical Engineering and Technology, Zhejiang University of Technology.

1. Radical-Triggered Tandem Reaction of Vinyl Azides with Isopropylxanthic Disulfide for the Synthesis of 6-Sulfanylmethyl Phenanthridines.PDF(2832KB)

Abstract

An 2,2'-azobis(2-methylpropionitrile) (AIBN) initiated tandem reaction of vinyl azides with isopropylxanthic disulfide to construct C-S/C-N bonds was disclosed. A range of functionalized 6-sulfanylmethyl phenanthridines could be easily accessed in 50%~84% yields with a good regioselectivity. The mechanism study indicates a free radical pathway in this reaction.

Key words: vinyl azides, isopropylxanthic disulfide, phenanthridine, radical reaction

Cite this article

Lu Lulu, Zhou Bingwei, Jin Hongwei, Liu Yunkui. Radical-Triggered Tandem Reaction of Vinyl Azides with Isopropylxanthic Disulfide for the Synthesis of 6-Sulfanylmethyl Phenanthridines[J]. Chin. J. Org. Chem., 2019, 39(2): 515-520.

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烯基叠氮与二异丙基黄原酸酯的自由基串联反应:合成6-巯甲基菲啶

Radical-Triggered Tandem Reaction of Vinyl Azides with Isopropylxanthic Disulfide for the Synthesis of 6-Sulfanylmethyl Phenanthridines

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