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

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 44期

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

页码：8814 / 8821

页数：8

共 31 条

[1] Catalytic Functionalization of Indoles in a New Dimension [J].

Bandini, Marco ;

Eichholzer, Astrid .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (51) :9608-9644

[2] Organocatalytic strategies for the asymmetric functionalization of indoles [J].

Bartoli, Giuseppe ;

Bencivenni, Giorgio ;

Dalpozzo, Renato .

CHEMICAL SOCIETY REVIEWS, 2010, 39 (11) :4449-4465

[3] VIBRINDOLE-A, A METABOLITE OF THE MARINE BACTERIUM, VIBRIO-PARAHAEMOLYTICUS, ISOLATED FROM THE TOXIC MUCUS OF THE BOXFISH OSTRACION-CUBICUS [J].

BELL, R ;

CARMELI, S ;

SAR, N .

JOURNAL OF NATURAL PRODUCTS-LLOYDIA, 1994, 57 (11) :1587-1590

[4] Synthesis and functionalization of Indoles through palladium-catalyzed reactions [J].

Cacchi, S ;

Fabrizi, G .

CHEMICAL REVIEWS, 2005, 105 (07) :2873-2920

[5] Industrial Oxidations with Organocatalyst TEMPO and Its Derivatives [J].

Ciriminna, Rosaria ;

Pagliaro, Mario .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2010, 14 (01) :245-251

[6]

DILBER S, 1989, PHARMAZIE, V44, P649

[7] Trimerisation of indole through laccase catalysis [J].

Ganachaud, Chrystelle ;

Garfagnoli, Vanessa ;

Tron, Thierry ;

Iacazio, Gilles .

TETRAHEDRON LETTERS, 2008, 49 (15) :2476-2478

[8] TYRPHOSTINS .2. HETEROCYCLIC AND ALPHA-SUBSTITUTED BENZYLIDENEMALONONITRILE TYRPHOSTINS AS POTENT INHIBITORS OF EGF RECEPTOR AND ERBB2/NEU TYROSINE KINASES [J].

GAZIT, A ;

OSHEROV, N ;

POSNER, I ;

YAISH, P ;

PORADOSU, E ;

GILON, C ;

LEVITZKI, A .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (06) :1896-1907

[9] POLYMERIZATION OF INDOLE .2. A NEW INDOLE TRIMER [J].

ISHII, H ;

MURAKAMI, K ;

SAKURADA, E ;

HOSOYA, K ;

MURAKAMI, Y .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (08) :2377-2385

[10] Transition Metal-Catalysed, Direct and Site-Selective N1-, C2-or C3-Arylation of the Indole Nucleus: 20 Years of Improvements [J].

Joucla, Lionel ;

Djakovitch, Laurent .

ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (05) :673-714

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