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2022 , Vol. 42 >Issue 7: 2155 - 2163

DOI: https://doi.org/10.6023/cjoc202201036

研究论文

路易斯酸促进的不饱和酰胺的分子内亲核加成杂环化反应合成2-噁唑啉衍生物及其在细胞成像中的应用

  • 陈学荣 ,
  • 祁亮 ,
  • 黄晋培 ,
  • 朱伟伟 ,
  • 周益峰
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  • a中国计量大学生命科学学院 杭州 310018
    b中山大学药学院 广州 510006
† 共同第一作者

收稿日期: 2022-01-22

  修回日期: 2022-02-17

  网络出版日期: 2022-04-11

基金资助

国家自然科学基金(22108264)

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Lewis Acid Promoted Intramolecular Nucleophilic Heterocyclization of Unsaturated Amides for the Synthesis of 2-Oxazolines and Their Applications in Imaging of Living Cells

  • Xuerong Chen ,
  • Liang Qi ,
  • Jinpei Huang ,
  • Weiwei Zhu ,
  • Yifeng Zhou
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  • aCollege of Life Sciences, China Jiliang University, Hangzhou 310018
    bSchool of Pharmaceutical Sciences, Sun Yat-Sen University, Guangzhou 510006
† These authors contributed equally to this work
* E-mail: ;

Received date: 2022-01-22

  Revised date: 2022-02-17

  Online published: 2022-04-11

Supported by

National Natural Science Foundation of China(22108264)

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摘要

2-噁唑啉及其衍生物是有机合成、材料化学和生物医药中重要的有机结构单元. 报道了一种高效、反应条件温和且无金属参与的路易斯酸促进的分子内亲核杂环化反应合成2-噁唑啉衍生物的方法(80%~94%分离产率), 并将合成得到的噁唑啉衍生物用于细胞成像研究, 结果表明, 合成的噁唑啉衍生物在细胞成像实验中表现出了良好的细胞相容性和成像性.

关键词： 路易斯酸; 杂环化; 2-噁唑啉; 细胞成像

本文引用格式

陈学荣 , 祁亮 , 黄晋培 , 朱伟伟 , 周益峰 . 路易斯酸促进的不饱和酰胺的分子内亲核加成杂环化反应合成2-噁唑啉衍生物及其在细胞成像中的应用[J]. 有机化学, 2022 , 42(7) : 2155 -2163 . DOI: 10.6023/cjoc202201036

Abstract

2-Oxazolines and their derivatives are important scaffolds present in the fields of organic synthesis, material science and biomedicine. An efficient, mild and metal-free process to synthesize 2-oxazoline derivatives was reported. Various 2-oxazoline derivatives were synthesized through the Lewis acid-mediated intramolecularly nucleophilic heterocyclization of unsaturated amides in high to excellent yields (80%~94% isolated yields). Besides, the experiments of imaging of living cells were conducted to verify the proper fluorescence properties of the 2-oxazoline derivative. The results indicated that the probe had good cellular compatibility, as well as the potential to track spatial dynamics in living cells.

Key words： Lewis acid; gheterocyclization; 2-oxazoline; cell imaging

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