Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (6): 2374-2383.DOI: 10.6023/cjoc202012040 Previous Articles     Next Articles



刘金妮a, 谢益碧a, 阳青青a, 黄年玉b, 王龙a,*()   

  1. a 三峡大学材料与化工学院 无机非金属晶体与能量转换材料重点实验室 湖北宜昌 443002
    b 三峡大学生物与制药学院 天然产物研究与利用湖北省重点实验室 湖北宜昌 443002
  • 收稿日期:2020-12-23 修回日期:2021-02-20 发布日期:2021-03-12
  • 通讯作者: 王龙
  • 基金资助:
    国家自然科学基金(21602123); 国家自然科学基金(21702001); 高等学校学科创新引智计划(111计划); 高等学校学科创新引智计划(D20015)

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 Liua, Yibi Xiea, Qingqing Yanga, Nianyu Huangb, Long Wanga()   

  1. 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
  • Received:2020-12-23 Revised:2021-02-20 Published:2021-03-12
  • Contact: Long Wang
  • 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)

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