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2021 , Vol. 41 >Issue 7: 2788 - 2799

DOI: https://doi.org/10.6023/cjoc202101024

研究论文

4-羟基香豆素在四氢喹啉及二香豆素内盐合成中的应用

  • 杨晓宇 ,
  • 柳建林 ,
  • 胡方芝 ,
  • 孙红梅 ,
  • 王亮 ,
  • 李帅帅
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  • a 青岛农业大学化学与药学院 山东青岛 266109
    b 青岛科技大学化学与分子工程学院 山东青岛 266042
† 共同第一作者(These authors contributed equally to this work).

收稿日期: 2021-01-16

  修回日期: 2021-03-23

  网络出版日期: 2021-04-12

基金资助

国家自然科学基金(21978144); 国家自然科学基金(21702117); 国家自然科学基金(21776148); 山东省重点研发计划(2018GSF118224); 山东省重点研发计划(2019GSF108020); 山东省重点研发计划(2019RKB01027); 山东省青创科技计划(2019KJM002); 青岛科技大学开放基金(QUSTHX201916); 青岛科技大学开放基金(QUSTHX202004)

收起

Diverse Application of 4-Hydroxycoumarin in the Syntheses of Tetrahydroquinoline and Zwitterionic Biscoumarin Derivatives

  • Xiaoyu Yang ,
  • Jianlin Liu ,
  • Fangzhi Hu ,
  • Hongmei Sun ,
  • Liang Wang ,
  • Shuai-Shuai Li
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  • a College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao, Shandong 266109
    b College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao, Shandong 266042
* Corresponding authors. E-mail: ;

Received date: 2021-01-16

  Revised date: 2021-03-23

  Online published: 2021-04-12

Supported by

National Natural Science Foundation of China(21978144); National Natural Science Foundation of China(21702117); National Natural Science Foundation of China(21776148); Key Research & Development Program of Shandong Province(2018GSF118224); Key Research & Development Program of Shandong Province(2019GSF108020); Key Research & Development Program of Shandong Province(2019RKB01027); Support Plan on Science and Technology for Youth Innovation of Universities in Shandong Province(2019KJM002); Opening Funding of Qingdao University of Science & Technology(QUSTHX201916); Opening Funding of Qingdao University of Science & Technology(QUSTHX202004)

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摘要

以4-羟基香豆素和邻胺基苯甲醛为原料, 高效合成了具有药物活性的3-位邻羟基苯甲酰基单取代的四氢喹啉衍生物. 在乙醇溶剂中, 反应经过克脑文格尔缩合/[1,5]-氢迁移/环化/水解/脱羧这五个串联过程进行. 另外, 还实现了底物控制的多样性合成, 在无催化剂、无溶剂、室温条件下制备了一系列二香豆素内盐.

关键词： 4-羟基香豆素; 氢迁移反应; 四氢喹啉; 二香豆素内盐

本文引用格式

杨晓宇 , 柳建林 , 胡方芝 , 孙红梅 , 王亮 , 李帅帅 . 4-羟基香豆素在四氢喹啉及二香豆素内盐合成中的应用[J]. 有机化学, 2021 , 41(7) : 2788 -2799 . DOI: 10.6023/cjoc202101024

Abstract

The pharmaceutically significant 3-mono-substituted tetrahydroquinoline derivatives carryingortho-hydroxy- benzoyl moiety are constructed via EtOH mediated cascade Knoevenagel condensation/[1,5]-hydride transfer/cyclization/hydrolysis/decarboxylation from 4-hydroxycoumarins ando-aminobenzaldehydes. In addition, the substrate-controlled diverse syntheses also could be achieved, and a variety of the zwitterionic biscoumarin derivatives are facilely provided under catalyst- and solvent-free conditions at room temperature.

Key words： 4-hydroxycoumarin; hydride-transfer reaction; tetrahydroquinoline; zwitterionic biscoumarin

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