[1]于金涛,滕建刚,李伊婷.铜催化活性烯烃与3-氨基吲唑反应合成芳氰基取代2-吲哚酮化合物[J].常州大学学报(自然科学版),2022,34(03):37-46.[doi:10.3969/j.issn.2095-0411.2022.03.006]
　YU Jintao,TENG Jiangang,LI Yiting.Copper-Catalyzed Synthesis of Cyanoarylated Oxindoles from Activated Alkenes and 3-Aminoindazoles[J].Journal of Changzhou University(Natural Science Edition),2022,34(03):37-46.[doi:10.3969/j.issn.2095-0411.2022.03.006]
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铜催化活性烯烃与3-氨基吲唑反应合成芳氰基取代2-吲哚酮化合物()
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常州大学学报(自然科学版)[ISSN:2095-0411/CN:32-1822/N]

卷:
第34卷
期数:
2022年03期
页码:
37-46
栏目:
化学化工
出版日期:
2022-05-28

文章信息/Info

Title:
Copper-Catalyzed Synthesis of Cyanoarylated Oxindoles from Activated Alkenes and 3-Aminoindazoles
文章编号:
2095-0411(2022)03-0037-10
作者:
于金涛; 滕建刚; 李伊婷
(常州大学石油化工学院,江苏常州213164)
Author(s):
YU Jintao;  TENG Jiangang;  LI Yiting
(School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China)
关键词:
2-吲哚酮;  脱氮开环;  3-氨基吲唑;  铜催化;  自由基反应
Keywords:
oxindole;  denitrogenative ring-opening reaction;  3-aminoindazole;  Cu-catalyzed;  radical reaction
分类号:
O 626.1
DOI:
10.3969/j.issn.2095-0411.2022.03.006
文献标志码:
A
摘要:
开发了铜催化的3-氨基吲唑与N-甲基-N-芳基甲基丙烯酰胺的反应,并以中等到良好的收率得到一系列3-位芳氰基取代的2-吲哚酮化合物。该反应是通过对丙烯酰胺结构中活性碳碳双键的双芳基化实现的,涉及自由基加成反应、环化反应过程,高效构建2-吲哚酮骨架结构。其中,3-氨基吲唑经历氧化脱氮开环反应得到的2-氰基芳基自由基是本反应的关键中间体。该反应的特点还包括起始原料易得、操作简便、一锅法同时实现了2个C—N键的断裂和2个C—C键的构建。
Abstract:
A copper-catalyzed dual arylation of the activated carbon-carbon double bonds in N-methyl-N-phenylmethacrylamide with 3-aminoindazoles was developed. A series of cyanoarylated oxindoles were obtained in moderate to good yields via cascade radical addition and cyclization processes. The reaction is realized by the double arylation of the activated carbon-carbon double bond in the acrylamide structure, and involves the process of radical addition reaction and cyclization reaction, and the 2-indolinone skeleton structure is efficiently constructed. Notably, 2-cyanophenyl radical, derived from denitrogenative ring-opening of 3-aminoindazole was the crucial intermediate. The feature of this reaction also includes the availability of starting materials, the cleavage of two C—N bonds and the construction of two C—C bonds in one-pot.

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备注/Memo

备注/Memo:
收稿日期: 2022-02-03。
基金项目: 国家自然科学基金资助项目(21672028)。
作者简介: 于金涛(1984—), 女, 山东聊城人, 博士, 副教授。E-mail: yujintao@cczu.edu.cn
更新日期/Last Update: 1900-01-01