Citation: Xu-Xu Qing-Feng, Huang Xian-Yun, Zhang Xiao, You Shu-Li. Synthesis of 1, 2-Dihydroquinolines by Reduction of Quinolines with Sodium Cyanoborohydride[J]. Chinese Journal of Organic Chemistry, ;2020, 40(10): 3446-3451. doi: 10.6023/cjoc202004015 shu

Synthesis of 1, 2-Dihydroquinolines by Reduction of Quinolines with Sodium Cyanoborohydride

a.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
b.
School of Pharmacy, East China University of Science and Technology, Shanghai 200237

Corresponding author: You Shu-Li, slyou@sioc.ac.cn
Received Date: 10 April 2020
Revised Date: 9 May 2020
Available Online: 15 May 2020
Fund Project: the National Natural Science Foundation of China 21821002the Ministry of Science and Technology of China 2016YFA0202900Project supported by the Ministry of Science and Technology of China (No. 2016YFA0202900) and the National Natural Science Foundation of China (No.21821002)

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An efficient conversion of quinolines to 1, 2-dihydroquinolines (50%~96% yield) was developed via the modification of the known methods. It was found that using sodium cyanoborohydride as a reductant would overcome the low conversion often encountered in previous studies. A series of N-alkoxycarbonyl-1, 2-dihydroquinolines were obtained through reduction of activated quinolium salts. Notably, with the exception of the 3-and 4-substituted substrates, a mixture of 1, 2-dihydro-quinolines and the over reduced tetrahydroquinolines was obtained with the ratio over 4:1. Besides, compared to the established methods, an easy operation without using large excess of chloroformate further enhances practicability of the methodology.
- quinoline,
- 1, 2-dihydroquinoline,
- dearomatization,
- sodium cyanoborohydride
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