有机化学 ›› 2020, Vol. 40 ›› Issue (3): 688-693.DOI: 10.6023/cjoc201909021 上一篇    下一篇

研究论文

钌(II)-催化偶氮苯与乙醛酸乙酯的环化反应构建3-羧酸酯吲唑

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 E-mail:chenxunchenpei@163.com
  • 基金资助:
    海南省科协青年科技英才学术创新计划(No.QCXM201808)和海南省自然科学基金(No.819QN227)资助项目.

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).

报道了一种简便有效的Ru(II)催化偶氮苯与乙醛酸乙酯的高选择性[4+1]环化反应,该反应历程涉及C—H键的活化.这种策略能够以中等至良好的产率去高效构建多样性的吲唑骨架结构.同时研究了该反应的动力学同位素效应,实验结果表明C—H键活化可能不属于整个反应历程的决速步骤.

关键词: 钌(II), C—H键活化, 环化反应, 吲唑

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