Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (3): 688-693.DOI: 10.6023/cjoc201909021 Previous Articles     Next Articles


陈训a,b, 王颖b, 王烁今a,b, 孔杜林b, 文丽君b, 翟锐锐b, 赵珂b, 白丽丽b, 李友宾a   

  1. a 海南医学院 热带转化医学教育部重点实验室 海南省热带药用植物研究开发重点实验室 海口 571199;
    b 海南医学院药学院 海口 571199
  • 收稿日期:2019-09-15 修回日期:2019-11-04 发布日期:2020-04-02
  • 通讯作者: 陈训
  • 基金资助:

Synthesis of 3-Carboxylate Indazoles via Ru(II)-Catalyzed Annulation of Azobenzenes with Ethyl Glyoxalate

Chen Xuna,b, Wang Yingb, Wang Shuojina,b, Kong Dulinb, Wen Lijunb, Zhai Ruiruib, Zhao Keb, Bai Lilib, Li Youbina   

  1. a Key Laboratory of Tropical Translational Medicine of Ministry of Education, Hainan Key Laboratory for Research and Development of Tropical Herbs, Hainan Medical University, Haikou 571199;
    b School of Pharmacy, Hainan Medical University, Haikou 571199
  • Received:2019-09-15 Revised:2019-11-04 Published:2020-04-02
  • Supported by:
    Project supported by the Program of Hainan Association for Science and Technology Plans to Youth R&D Innovation (No. QCXM201808) and the Natural Science Foundation of Hainan Province (No. 819QN227).

The Ru(II)-catalyzed regioselective[4+1] cycloaddition of azobenzenes with ethyl glyoxalate through C-H bond activation has been developed. This method provides a facile approach to various 3-carboxylate indazoles in moderate to good yields. Meantime, the kinetic isotope effect was further investigated and the results indicated that the C-H bond-breaking was possibly not involved in the rate-limiting step of this transformation.

Key words: Ru (II), C—H bond activation, cycloaddition, Indazoles