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

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

研究论文

氰基硼氢化钠还原喹啉合成1,2-二氢喹啉

  • 徐徐清风 ,
  • 黄显韵 ,
  • 张霄 ,
  • 游书力
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  • a 中国科学院上海有机化学研究所 金属有机化学国家重点实验室 上海 200032;
    b 华东理工大学药学院 上海 200237

收稿日期: 2020-04-10

  修回日期: 2020-05-09

  网络出版日期: 2020-05-15

基金资助

国家科技计划（No.2016YFA0202900）和国家自然科学基金（No.21821002）资助项目.

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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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摘要

1，2-二氢喹啉是一类重要的化合物.通过对已有方法的改进，发展了一类从喹啉出发高效合成1，2-二氢喹啉的反应（产率50%～96%）.通过对一系列还原剂的筛选发现，当使用氰基硼氢化钠作为还原剂时，能有效克服已有方法中低转化率的问题，实现被活化的喹啉盐经还原去芳构化反应得到一系列N-烷氧羰基取代的1，2-二氢喹啉.需要指出的是，除3-位或4-位含有取代基的底物能得到单一的目标产物外，其他底物都会生成过度还原的四氢喹啉副产物，二氢喹啉与四氢喹啉比例均大于4：1.同时，该方法相较于文献中的方法操作简便，无须使用大大过量的氯甲酸酯，增强了反应的实用性.

关键词： 喹啉; 1,2-二氢喹啉; 去芳构化; 氰基硼氢化钠

本文引用格式

徐徐清风 , 黄显韵 , 张霄 , 游书力 . 氰基硼氢化钠还原喹啉合成1,2-二氢喹啉[J]. 有机化学, 2020 , 40(10) : 3446 -3451 . DOI: 10.6023/cjoc202004015

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

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