Citation: 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. doi: 10.6023/cjoc201909021 shu

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

Corresponding author: Chen Xun, chenxunchenpei@163.com
Received Date: 15 September 2019
Revised Date: 4 November 2019
Available Online: 21 November 2019
Fund Project: the Program of Hainan Association for Science and Technology Plans to Youth R & D Innovation QCXM201808the Natural Science Foundation of Hainan Province 819QN227Project 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)

Figures(4)

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.
- Ru (Ⅱ),
- C—H bond activation,
- cycloaddition,
- Indazoles
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