Tetrabutylammonium Iodide-Catalyzed Radical Alkoxycarbonylation of Activated Alkenes: Synthesis of Isoquinolinedione Derivatives

doi:10.6023/cjoc201410015

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (4): 875-881.DOI: 10.6023/cjoc201410015 Previous Articles Next Articles

ARTICLE

四丁基碘化胺催化活化烯烃烷氧羰基化反应:合成异喹啉二酮衍生物

唐裕才, 张敏, 李小青, 许响生, 杜晓华

浙江工业大学化学工程学院杭州 310014

收稿日期:2014-10-11 修回日期:2014-11-19 发布日期:2014-12-02
通讯作者: 杜晓华 E-mail:duxiaohua@zjut.edu.cn
基金资助:
国家自然科学基金(No. 21102130)和浙江省科技创新团队(Nos. 2010R50018, 2011R50017)资助项目.

Tetrabutylammonium Iodide-Catalyzed Radical Alkoxycarbonylation of Activated Alkenes: Synthesis of Isoquinolinedione Derivatives

Tang Yucai, Zhang Min, Li Xiaoqing, Xu Xiangsheng, Du Xiaohua

College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014

Received:2014-10-11 Revised:2014-11-19 Published:2014-12-02
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21102130) and the Key Innovation Team of Science & Technology in Zhejiang Province (Nos. 2010R50018, 2011R50017).

1. Tetrabutylammonium Iodide-Catalyzed Radical Alkoxycarbonylation of Activated Alkenes: Synthesis of Isoquinolinedione Derivatives.PDF(3197KB)

Abstract

The isoquinolinedione skeletons are important building blocks, which have been widely present in plant alkaloids, natural products and pharmaceuticals. In this paper, a novel method to construct isoquinolinedione framework was developed, which can be easily operated under metal-free conditions. In the presence of tetrabutylammonium-iodide catalyst, hydrogen atoms were abstracted step by step from carbazate to generate methoxycarbonyl radical which followed by radical addition/cyclization reaction leading to isoquinolinedione. The presented methodology will provide new strategies for construct isoquinolinedione-type products, which has advantages of simple operation, mild reaction conditions, and environmentally benign.

Key words: isoquinolinedione skeleton, metal-free, tetrabutylammonium-iodide, radical addition/cyclization

Cite this article

Tang Yucai, Zhang Min, Li Xiaoqing, Xu Xiangsheng, Du Xiaohua. Tetrabutylammonium Iodide-Catalyzed Radical Alkoxycarbonylation of Activated Alkenes: Synthesis of Isoquinolinedione Derivatives[J]. Chin. J. Org. Chem., 2015, 35(4): 875-881.

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四丁基碘化胺催化活化烯烃烷氧羰基化反应:合成异喹啉二酮衍生物

Tetrabutylammonium Iodide-Catalyzed Radical Alkoxycarbonylation of Activated Alkenes: Synthesis of Isoquinolinedione Derivatives

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