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Chinese Journal of Organic Chemistry >

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

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

ARTICLES

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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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

Cite this article

Jingpeng Li , Shuntao Huang , Qi Yang , Weiqiang Li , Teng Liu , Chao Huang . A Practical Synthesis of (Z)-N-Vinyl Substituted N,O-Acetals under Continuous Flow Technology[J]. Chinese Journal of Organic Chemistry, 2023 , 43(4) : 1550 -1558 . DOI: 10.6023/cjoc202208016

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