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2024 , Vol. 44 >Issue 12: 3727 - 3738

DOI: https://doi.org/10.6023/cjoc202405040

研究论文

有机磷酸催化的[3＋3]环化反应合成茚并喹啉二酮衍生物

  • 郭昕彦 ,
  • 于浩磊 ,
  • 万洪林 ,
  • 陆钰 ,
  • 谭伟 ,
  • 石枫
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  • a 江苏师范大学化学与材料科学学院 江苏徐州 221116
    b 常州大学石油化工学院 江苏常州 213164
†共同第一作者.

收稿日期: 2024-05-28

  修回日期: 2024-07-30

  网络出版日期: 2024-09-02

基金资助

国家自然科学基金(22125104); 国家自然科学基金(22301112); 江苏省自然科学基金(BK20210916); 本科生创新项目(202410320104Y); 本科生创新项目(XSJCX14139); 江苏省优秀科技创新团队资助项目.

收起

Organophosphoric Acid Catalyzed [3＋3] Cyclization for the Synthesis of Indenoquinolinedione Derivatives

  • Xinyan Guo ,
  • Haolei Yu ,
  • Honglin Wan ,
  • Yu Lu ,
  • Wei Tan ,
  • Feng Shi
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  • a School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116
    b School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213164
†These authors contributed equally to this work.
*Corresponding authors. E-mail:;

Received date: 2024-05-28

  Revised date: 2024-07-30

  Online published: 2024-09-02

Supported by

National Natural Science Foundation of China(22125104); National Natural Science Foundation of China(22301112); Natural Science Foundation of Jiangsu Province(BK20210916); Undergraduate Students Innovative Project(202410320104Y); Undergraduate Students Innovative Project(XSJCX14139); Project for Excellent Scientific and Technological Innovation Team of Jiangsu Province.

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摘要

实现了有机磷酸催化下2-亚芳基茚-1,3-二酮与烯胺酮的[3＋3]环化反应, 以中等至优异的产率合成了一系列结构多样的茚并喹啉二酮衍生物. 该反应具有反应条件温和、催化剂容易获得及底物范围宽等优点. 该工作不仅为构建具有重要生物活性的1,4-二氢吡啶骨架提供了一种有效的方法, 而且提出了一种可能的反应途径和活化模式, 丰富了有机磷酸催化和[3＋3]环化反应的研究内容.

关键词： 有机磷酸; [3＋3]环化; 有机催化; 烯胺酮; 1,4-二氢吡啶

本文引用格式

郭昕彦 , 于浩磊 , 万洪林 , 陆钰 , 谭伟 , 石枫 . 有机磷酸催化的[3＋3]环化反应合成茚并喹啉二酮衍生物[J]. 有机化学, 2024 , 44(12) : 3727 -3738 . DOI: 10.6023/cjoc202405040

Abstract

An organophosphoric acid catalyzed [3＋3] cyclization of 2-arylidene-indan-1,3-diones with enaminones has been established, which afforded a series of structurally diverse indenoquinolinedione derivatives in moderate to excellent yields. This [3＋3] cyclization has some advantages such as mild reaction conditions, readily available catalyst and wide substrate range. This work not only provides an efficient method for constructing biologically important 1,4-dihydropyridine motif, but also suggests a possible reaction pathway and activation mode, therefore enriching the research contents of organophosphoric acid catalysis and [3＋3] cyclization reactions.

Key words： organophosphoric acid; [3＋3] cyclization; organocatalysis; enaminone; 1,4-dihydropyridine

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