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



唐裕才, 张敏, 李小青, 许响生, 杜晓华   

  1. 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
  • 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   

  1. 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).

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