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

doi:10.6023/cjoc201909021

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

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

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 Xun^a,b, Wang Ying^b, Wang Shuojin^a,b, Kong Dulin^b, Wen Lijun^b, Zhai Ruirui^b, Zhao Ke^b, Bai Lili^b, Li Youbin^a

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).

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Abstract

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

Cite this article

Chen Xun, Wang Ying, Wang Shuojin, Kong Dulin, Wen Lijun, Zhai Ruirui, Zhao Ke, Bai Lili, Li Youbin. Synthesis of 3-Carboxylate Indazoles via Ru(II)-Catalyzed Annulation of Azobenzenes with Ethyl Glyoxalate[J]. Chinese Journal of Organic Chemistry, 2020, 40(3): 688-693.

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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

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

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