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2023 , Vol. 43 >Issue 4: 1550 - 1558

DOI: https://doi.org/10.6023/cjoc202208016

研究论文

利用连续流动技术合成(Z)-N-乙烯基取代N,O-缩醛

  • 李靖鹏 ,
  • 黄顺桃 ,
  • 杨棋 ,
  • 李伟强 ,
  • 刘腾 ,
  • 黄超
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  • a 曲靖师范学院化学与环境科学学院 云南曲靖 655011
    b 云南民族大学化学与环境学院 生物基材料绿色制备技术国家地方联合工程研究中心 昆明 650500

收稿日期: 2022-08-15

  修回日期: 2022-09-30

  网络出版日期: 2022-11-22

基金资助

国家自然科学基金(21662046); 国家自然科学基金(21202142); 云南省教育厅科研基金(2021Y667); 及云南地方高校科研基金(202101BA070001-049)

收起

A Practical Synthesis of (Z)-N-Vinyl Substituted N,O-Acetals under Continuous Flow Technology

  • Jingpeng Li ,
  • Shuntao Huang ,
  • Qi Yang ,
  • Weiqiang Li ,
  • Teng Liu ,
  • Chao Huang
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  • a College of Chemistry and Environmental Science, Qujing Normal University, Qujing, Yunnan 655011
    b National and Local Joint Engineering Research Center for Green Preparation Technology of Biobased Materials, School of Chemistry and Environment, Yunnan Minzu University, Kunming 650500
* Corresponding author. ;

Received date: 2022-08-15

  Revised date: 2022-09-30

  Online published: 2022-11-22

Supported by

National Natural Science Foundation of China(21662046); National Natural Science Foundation of China(21202142); Scientific Research Fund of Yunnan Provincial Department of Education(2021Y667); Yunnan Local Colleges Research Projects of China(202101BA070001-049)

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摘要

利用连续流动技术发展了一种新颖、高效且实用的制备(Z)-N-乙烯基五元环N,O-缩醛衍生物的方法. 该串联环化反应以席夫碱亚胺作为中间体, 随后在碱的作用下羟基与炔酯加成, 经历一个独特的分子内重排, 合成了缩醛衍生物. 整个级联环化过程生成了一个新的C—O键和C—N键. 此外, 与传统批量反应相比, 连续流动技术的运用可精准控制三组分反应途径, 抑制两组分副产物的生成, 并能在较短时间内以较高收率(81%~90%)得到一系列结构多样的含氮和含氧杂环分子.

关键词： 环状N,O-缩醛; 串联环化反应; 控制反应途径; 连续流动合成; 三组分反应

本文引用格式

李靖鹏 , 黄顺桃 , 杨棋 , 李伟强 , 刘腾 , 黄超 . 利用连续流动技术合成(Z)-N-乙烯基取代N,O-缩醛[J]. 有机化学, 2023 , 43(4) : 1550 -1558 . DOI: 10.6023/cjoc202208016

Abstract

A novel, efficient and practical route to the preparation of (Z)-N-vinyl five-membered cyclic N,O-acetal derivatives utilized by continuous flow technology has been developed. The tandem cyclization reaction uses Schiff base imine as an intermediate, followed by the addition of hydroxyl group to alkynyl ester under the action of alkali, undergoing a unique intramolecular rearrangement to synthesize acetal derivatives. The whole cascade cyclization process generates a new C—O bond and C—N bond. In addition, the application of continuous flow technology can accurately control the three-component reaction pathway compared with traditional batch reaction, which can inhibit the generation of by-products between two components and provide a series of structurally diverse nitrogen- and oxygen-containing heterocycles in short time with high yields (81%~90%).

Key words： cyclic N,O-acetal; cascade cyclization reaction; control reaction pathway; continuous flow technology; three- component reaction

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