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

doi:10.6023/cjoc201905006

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (12): 3524-3531.DOI: 10.6023/cjoc201905006 Previous Articles Next Articles

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^a, 罗清^a, 陈春琳^a, 盈凤元^a, 董英^b, 刘颖杰^c, 王宝玲^d, 马银海^a, 梁德强^a,d

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 发布日期:2019-08-01
通讯作者: 刘颖杰, 梁德强 E-mail:liuyj691@nenu.edu.cn;liangdq695@nenu.edu.cn
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.

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

Dai Enrui^a, Luo Qing^a, Chen Chunlin^a, Ying Fengyuan^a, Dong Ying^b, Liu Yingjie^c, Wang Baoling^d, Ma Yinhai^a, Liang Deqiang^a,d

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:2019-05-05 Revised:2019-07-02 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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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

Cite this article

Dai Enrui, Luo Qing, Chen Chunlin, Ying Fengyuan, Dong Ying, Liu Yingjie, Wang Baoling, Ma Yinhai, Liang Deqiang. Copper-Catalyzed Cyanoisopropylalkenylation of N-Alkenyl-acrylamides to Give 1,3-Dihydropyrrol-2-ones[J]. Chinese Journal of Organic Chemistry, 2019, 39(12): 3524-3531.

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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

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

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