研究论文

布朗斯特酸催化合成亚砜亚胺基二氢吡喃酮类衍生物

  • 孙鑫浩 ,
  • 段学伦 ,
  • 宋汪泽 ,
  • 姜文凤
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  • 大连理工大学化工学院 辽宁大连 116024

收稿日期: 2021-08-12

  修回日期: 2021-10-08

  网络出版日期: 2022-02-24

基金资助

国家自然科学基金(21571027); 国家自然科学基金(21978039); 中央高校基本科研业务费(DUT20YG120)

Brønsted Acid-Catalyzed the Synthesis of Sulfoximide Substituted Dihydropyranone Derivatives

  • Xinhao Sun ,
  • Xuelun Duan ,
  • Wangze Song ,
  • Wenfeng Jiang
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  • School of Chemical Engineering, Dalian University of Technology, Dalian, Liaoning 116024
* Corresponding authors. E-mail: ;

Received date: 2021-08-12

  Revised date: 2021-10-08

  Online published: 2022-02-24

Supported by

National Natural Science Foundation of China(21571027); National Natural Science Foundation of China(21978039); Fundamental Research Funds for the Central Universities(DUT20YG120)

摘要

亚砜亚胺基团和二氢吡喃酮结构均具有潜在的生物活性, 但目前尚无制备亚砜亚胺基取代的二氢吡喃酮类衍生物的方法. 开发了一种使用磷酸二苯酯作为布朗斯特酸催化剂, 通过亚砜亚胺和二氢吡喃酮的亲核取代反应, 合成亚砜亚胺基取代的二氢吡喃酮类衍生物的新方法, 收率为44%~78%. 该方法条件温和、操作简单且官能团兼容性好, 无需传统方法中使用的贵金属催化剂, 为糖苷类化合物的合成提供了一种新颖高效的策略.

本文引用格式

孙鑫浩 , 段学伦 , 宋汪泽 , 姜文凤 . 布朗斯特酸催化合成亚砜亚胺基二氢吡喃酮类衍生物[J]. 有机化学, 2022 , 42(2) : 487 -497 . DOI: 10.6023/cjoc202108015

Abstract

Both sulfoximide and dihydropyranone derivatives have potential bioactivities. However, it is still undisclosed to prepare sulfoximide-substituted dihydropyranone derivatives. Herein, diphenyl phosphate, as Brønsted acid was used to catalyze the nucleophilic substitution reactions of sulfoximides and dihydropyranones to afford sulfoximide substituted dihydropyranone derivatives in 44%~78% yields. This method features mild conditions, simple operation and good functional group compatibility, which avoids using noble metals in traditional manners and provides a novel and effective strategy for the synthesis of glycosides.

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