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2019 , Vol. 39 >Issue 12: 3524 - 3531

DOI: https://doi.org/10.6023/cjoc201905006

研究论文

铜催化N-烯基丙烯酰胺氰异丙基化/烯基化反应合成1,3-二氢吡咯-2-酮

  • 戴恩睿 ,
  • 罗清 ,
  • 陈春琳 ,
  • 盈凤元 ,
  • 董英 ,
  • 刘颖杰 ,
  • 王宝玲 ,
  • 马银海 ,
  • 梁德强
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  • a 昆明学院化学化工学院 昆明 650214;
    b 山东师范大学化学化工与材料科学学院 济南 250014;
    c 哈尔滨商业大学药学院药物工程技术研究中心 哈尔滨 150076;
    d 云南省塑料薄膜制品工程技术研究中心 昆明 650214

收稿日期: 2019-05-05

  修回日期: 2019-07-02

  网络出版日期: 2019-08-01

基金资助

国家自然科学基金（No.21702083）、云南省万人计划青年拔尖人才专项、云南省高校科技创新团队支持计划、云南省应用基础研究计划项目（Nos.2018FD028，2018FH001-002）、黑龙江省自然科学基金优秀青年（No.YQ2019B004）、云南省教育厅资助性项目（No.2017ZDX048）和昆明学院人才引进（No.YJL19001）资助项目.

收起

Copper-Catalyzed Cyanoisopropylalkenylation of N-Alkenyl-acrylamides to Give 1,3-Dihydropyrrol-2-ones

  • Dai Enrui ,
  • Luo Qing ,
  • Chen Chunlin ,
  • Ying Fengyuan ,
  • Dong Ying ,
  • Liu Yingjie ,
  • Wang Baoling ,
  • Ma Yinhai ,
  • Liang Deqiang
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  • a Department of Chemistry, Kunming University, Kunming 650214;
    b College of Chemistry, Chemical Engineering and Materials Science, Shandong Normal University, Jinan 250014;
    c Engineering Research Center for Medicine, Harbin University of Commerce College of Pharmacy, Harbin 150076;
    d Yunnan Engineering Technology Research Center for Plastic Films, Kunming 650214

Received date: 2019-05-05

  Revised date: 2019-07-02

  Online published: 2019-08-01

Supported by

Project supported by the National Natural Science Foundation of China (No. 21702083), the Yunnan Ten Thousand Talent Program for Young Top-Notch Talents, the Program for Innovative Research Team (in Science and Technology) in Universities of Yunnan Province, the Applied Basic Research Programs of Yunnan Science and Technology Department (Nos. 2018FD028, 2018FH001-002), the Excellent Youth Project of Heilongjiang Natural Science Foundation (No. UNPYSCT-2016181), the Scientific Research Funds of Yunnan Education Department (No. 2017ZDX048) and the Research Foundation for Introduced Talents of Kunming University (No. YJL19001).

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摘要

报道了铜催化的化学选择性N-烯基丙烯酰胺氰异丙基化/环化级联反应，利用该反应可以实现1，3-二氢吡咯-2-酮的合成.丙烯酰胺的自由基环合反应中，用于捕获分子内自由基的基团主要局限于芳基、炔基和氰基，而本工作使用烯胺双键作为内置自由基捕获基团，以丙烯酰胺双键作为自由基受体.该反应的化学选择性可能是由自由基反应的极性匹配原则决定.

关键词： 烯酰胺; 烯烃; 偶氮化合物; 自由基反应; 铜

本文引用格式

戴恩睿 , 罗清 , 陈春琳 , 盈凤元 , 董英 , 刘颖杰 , 王宝玲 , 马银海 , 梁德强 . 铜催化N-烯基丙烯酰胺氰异丙基化/烯基化反应合成1,3-二氢吡咯-2-酮[J]. 有机化学, 2019 , 39(12) : 3524 -3531 . DOI: 10.6023/cjoc201905006

Abstract

A copper-catalyzed cyanoisopropylation/cyclization cascade of N-alkenylacrylamides is presented, providing a straightforward and chemoselective access to 1,3-dihydropyrrol-2-ones. In acrylamide-based radical cyclization, radical-trapping groups are mainly restricted to aryl, alkynyl or cyano group. But in this reaction, the enaminic double bond was used as an inbuilt radical trap, while the olefinic bond of the acrylamidyl moiety acted as the radical acceptor. Such chemoselectivity might be attributed to polarity matching.

Key words： enamide; alkene; azo compound; radical reaction; copper

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