有机化学 ›› 2021, Vol. 41 ›› Issue (7): 2788-2799.DOI: 10.6023/cjoc202101024 上一篇    下一篇

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a, 柳建林a, 胡方芝a, 孙红梅a, 王亮a,b,*(), 李帅帅a,b,*()   

  1. 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
  • 收稿日期:2021-01-16 修回日期:2021-03-23 发布日期:2021-04-12
  • 通讯作者: 王亮, 李帅帅
  • 作者简介:
    † 共同第一作者(These authors contributed equally to this work).
  • 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)

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

Xiaoyu Yanga, Jianlin Liua, Fangzhi Hua, Hongmei Suna, Liang Wanga,b(), Shuai-Shuai Lia,b()   

  1. 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
  • Received:2021-01-16 Revised:2021-03-23 Published:2021-04-12
  • Contact: Liang Wang, Shuai-Shuai Li
  • 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)

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

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