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Chinese Journal of Organic Chemistry >

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

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

ARTICLES

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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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

Cite this article

Xiaoyu Yang , Jianlin Liu , Fangzhi Hu , Hongmei Sun , Liang Wang , Shuai-Shuai Li . Diverse Application of 4-Hydroxycoumarin in the Syntheses of Tetrahydroquinoline and Zwitterionic Biscoumarin Derivatives[J]. Chinese Journal of Organic Chemistry, 2021 , 41(7) : 2788 -2799 . DOI: 10.6023/cjoc202101024

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