Synthesis of 3,3-disubstituted oxindoles by organoselenium-induced radical cyclizations of N-arylacrylamides

被引：10

作者：

Fu, Wei-jun ^{[1
]}

Zhu, Mei ^{[1
]}

Zou, Guang-long ^{[2
]}

机构：

[1] Luoyang Normal Univ, Coll Chem & Chem Engn, Luoyang 471022, Peoples R China

[2] Guizhou Minzu Univ, Sch Chem & Enviromental Sci, Guiyang 550025, Peoples R China

来源：

HETEROCYCLIC COMMUNICATIONS | 2015年 / 21卷 / 01期

基金：

中国国家自然科学基金;

关键词：

alkenes; cyclization; organoselenium; oxindole; radical cyclization; ACTIVATED ALKENES; FUNCTIONALIZATION;

D O I：

10.1515/hc-2014-0195

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and practical approach to oxindole derivatives via organoselenium-induced radical cyclizations of N-arylacrylamides has been developed. This method provides a convenient access to a variety of selenium-containing oxindoles in good to excellent yields under relatively mild reaction conditions. As one of its notable features, the radical process allows for the direct formation of a Se-C bond and the construction of a oxindole ring in one reaction.

引用

页码：9 / 12

页数：4

共 21 条

[1] Visible-Light-Mediated Radical Aryldifluoroacetylation of N-Arylacrylamides to give Difluoroacetylated Oxindoles
Fu, Weijun
Zhu, Mei
Zou, Guanglong
Xu, Chen
Wang, Zhiqiang
[J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 3 (12) : 1273 - 1276
[2] Visible-Light-Mediated Trifluoroethylation of N-Arylacrylamides with Trifluoroethyl Iodide: Synthesis of CF3-Containing Oxindoles
Fu, Weijun
Zhu, Mei
Zou, Guanglong
Xu, Chen
Wang, Zhiqiang
[J]. SYNLETT, 2014, 25 (17) : 2513 - 2517
[3] A Metal-Free Route to CF3-Containing Oxindoles by PhI(OAc)2-Mediated Trifluoromethylation of N-Arylacrylamides with TMSCF3
Fu, Weijun
Xu, Fengjuan
Fu, Yuqin
Xu, Chen
Li, Shihui
Zou, Dapeng
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (04) : 709 - 712
[4] Synthesis of 3,3-Disubstituted Oxindoles by Visible-Light-Mediated Radical Reactions of Aryl Diazonium Salts with N-Arylacrylamides
Fu, Weijun
Xu, Fengjuan
Fu, Yuqin
Zhu, Mei
Yu, Jiaqi
Xu, Chen
Zou, Dapeng
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (23) : 12202 - 12206
[5] Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents
Galliford, Chris V.
Scheidt, Karl A.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (46) : 8748 - 8758
[6] Transition-Metal-Mediated Routes to 3,3-Disubstituted Oxindoles through Anilide Cyclisation
Klein, Johannes E. M. N.
Taylor, Richard J. K.
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (34) : 6821 - 6841
[7] Synthesis of Sulfonated Oxindoles by Potassium Iodide Catalyzed Arylsulfonylation of Activated Alkenes with Sulfonylhydrazides in Water
Li, Xiaoqing
Xu, Xiangsheng
Hu, Peizhu
Xiao, Xuqiong
Zhou, Can
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (14) : 7343 - 7348
[8] Direct Annulations toward Phosphorylated Oxindoles: Silver-Catalyzed Carbon-Phosphorus Functionalization of Alkenes
Li, Ya-Min
Sun, Meng
Wang, Hong-Li
Tian, Qiu-Ping
Yang, Shang-Dong
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (14) : 3972 - 3976
[9] Metal-Free Radical Azidoarylation of Alkenes: Rapid Access to Oxindoles by Cascade CN and CC Bond-Forming Reactions
Matcha, Kiran
Narayan, Rishikesh
Antonchick, Andrey P.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (31) : 7985 - 7989
[10] Highly selective thioselenation of vinylcyclopropanes with a (PhS)2-(PhSe)2 binary system and its application to thiotelluration
Ogawa, A
Ogawa, I
Obayashi, R
Umezu, K
Doi, M
Hirao, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (01) : 86 - 92

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