Metal-free catalyzed oxidative trimerization of indoles by using TEMPO in air: a biomimetic approach to 2-(1H-indol-3-yl)-2,3′-biindolin-3-ones

被引:45
作者
Qin, Wen-Bing [1 ]
Chang, Qiong [1 ]
Bao, Yun-Hong [1 ]
Wang, Ning [1 ]
Chen, Zheng-Wang [1 ]
Liu, Liang-Xian [1 ]
机构
[1] Gannan Normal Univ, Dept Chem & Chem Engn, Ganzhou 341000, Jiangxi, Peoples R China
关键词
FUNCTIONALIZATION; POLYMERIZATION; ROUTES;
D O I
10.1039/c2ob26390d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple, convenient and efficient metal-free catalyzed oxidative trimeric reaction of indoles toward a variety of 2-(1H-indol-3-yl)-2,3'-biindolin-3-one derivatives in moderate to excellent yields has been developed. This transformation proceeds via a tandem oxidative homocoupling reaction by using TEMPO in air as an environmentally benign oxidant. This methodology provides an alternative approach for the direct generation of all-carbon quaternary centers at the C3 position of indoles.
引用
收藏
页码:8814 / 8821
页数:8
相关论文
共 31 条
[11]   Total Synthesis of (+)-Isatisine A [J].
Karadeolian, Avedis ;
Kerr, Michael A. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (06) :1133-1135
[12]  
Karadeoltan A, 2010, J ORG CHEM, V75, P6830, DOI [10.1021/jo101209y, 10.1021/jo101209v]
[13]   InCl3-Mediated Addition of Indole to Isatogens: An Expeditious Synthesis of 13-deoxy-Isatisine A [J].
Kumar, Chepuri V. Suneel ;
Puranik, Vedavati G. ;
Ramana, Chepuri V. .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (31) :9601-9611
[14]   Total Synthesis of (+)-Isatisine A [J].
Lee, Jihoon ;
Panek, James S. .
ORGANIC LETTERS, 2011, 13 (03) :502-505
[15]   Isatisine a, a novel alkaloid with an unprecedented skeleton from leaves of isatis indigotica [J].
Liu, Ji-Feng ;
Jiang, Zhi-Yong ;
Wang, Rui-Rui ;
Zheng, Yong-Tang ;
Chen, Ji-Jun ;
Zhang, Xue-Mei ;
Ma, Yun-Bao .
ORGANIC LETTERS, 2007, 9 (21) :4127-4129
[16]   Acid-promoted competing pathways in the oxidative polymerization of 5,6-dihydroxyindoles and related compounds: Straightforward cyclotrimerization routes to diindolocarbazole derivatives [J].
Manini, P ;
d'Ischia, M ;
Milosa, M ;
Prota, G .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (20) :7002-7008
[17]   Catalytic oxidation of organic substrates by molecular oxygen and hydrogen peroxide by multistep electron transfer -: A biomimetic approach [J].
Piera, Julio ;
Backvall, Jan-E. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (19) :3506-3523
[18]   Synthesis of symmetrical and unsymmetrical 3,3-di(indolyl)indolin-2-ones under controlled catalysis of ionic liquids [J].
Rad-Moghadam, Kurosh ;
Sharifi-Kiasaraie, Masoumeh ;
Taheri-Amlashi, Homayun .
TETRAHEDRON, 2010, 66 (13) :2316-2321
[19]   Asymmetric Bronsted Acid-Catalyzed Friedel-Crafts Reactions of Indoles with Cyclic Imines - Efficient Generation of Nitrogen-Substituted Quaternary Carbon Centers [J].
Rueping, Magnus ;
Raja, Sadiya ;
Nunez, Alberto .
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (04) :563-568
[20]   Organocatalytic oxidations mediated by nitroxyl radicals [J].
Sheldon, RA ;
Arends, IWCE .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) :1051-1071