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Chinese Journal of Organic Chemistry >

2021 , Vol. 41 >Issue 6: 2374 - 2383

DOI: https://doi.org/10.6023/cjoc202012040

ARTICLES

Ugi Four-Component Reaction Based on the in situ Capture of Amines and Subsequent Modification Tandem Cyclization Reaction: "One-Pot" Synthesis of Six- and Seven-Membered Heterocycles

  • Jinni Liu ,
  • Yibi Xie ,
  • Qingqing Yang ,
  • Nianyu Huang ,
  • Long Wang
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  • a Key Laboratory of Inorganic Nonmetallic Crystalline and Energy Conversion Materials, College of Materials and Chemical Engineering, China Three Gorges University, Yichang, Hubei 443002
    b Hubei Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Science, China Three Gorges University, Yichang, Hubei 443002
*Corresponding author.E-mail:

Received date: 2020-12-23

  Revised date: 2021-02-20

  Online published: 2021-03-12

Supported by

National Natural Science Foundation of China(21602123); National Natural Science Foundation of China(21702001); Programme of Introducing Talents of Discipline to Universities (111 Project(D20015)

Fold

Abstract

The tandem reaction strategy of Ugi four-component reaction and its subsequent modification reaction based on in situ capture of amines to prepare three types of six- and seven-membered nitrogen-heterocycles are reported. According to this strategy, amines were synthesized in situand immediately worked as the substrate for the Ugi four-component reaction reaction and subsequent modification tandem reaction. Starting from cheap and easily available nitro compounds, the application scope of substrates has been expanded and the problems of amines of easy oxidation, poor stability and versatility have been solved. Furthermore, due to the atom economy and versatility, the tandem reaction strategy has become a new approach for the synthesis of nitrogen-hete- rocycles. In addition, based on a series of conditional control experiments, a plausible mechanism for the reaction is proposed.

Key words： in situcapture of amines; Ugi four-component reaction /Wittig reaction; Ugi four-component reaction/Staudinger/aza-Wittig reaction; tandem reaction; one-pot synthesis; heterocycles

Cite this article

Jinni Liu , Yibi Xie , Qingqing Yang , Nianyu Huang , Long Wang . Ugi Four-Component Reaction Based on the in situ Capture of Amines and Subsequent Modification Tandem Cyclization Reaction: "One-Pot" Synthesis of Six- and Seven-Membered Heterocycles[J]. Chinese Journal of Organic Chemistry, 2021 , 41(6) : 2374 -2383 . DOI: 10.6023/cjoc202012040

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