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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 10: 3446 - 3451

DOI: https://doi.org/10.6023/cjoc202004015

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

  • Xu-Xu Qing-Feng ,
  • Huang Xian-Yun ,
  • Zhang Xiao ,
  • You Shu-Li
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  • 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

Received date: 2020-04-10

  Revised date: 2020-05-09

  Online published: 2020-05-15

Supported by

Project 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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Abstract

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.

Key words： quinoline; 1,2-dihydroquinoline; dearomatization; sodium cyanoborohydride

Cite this article

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

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