Facile regiospecific synthesis of 2,3-disubstituted indoles from isatins

被引：16

作者：

Dou, Xiaowei

Yao, Weijun

Wen, Shan

Lu, Yixin ^{[1
]}

机构：

[1] Natl Univ Singapore, Inst Life Sci, Dept Chem, Singapore 117543, Singapore

来源：

CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 67期

关键词：

NONREARRANGED MONOTERPENOID UNIT; N-ARYL ENAMINES; PALLADIUM-CATALYZED REACTIONS; C BOND FORMATION; INTERNAL ALKYNES; OXIDATIVE CYCLIZATION; EFFICIENT SYNTHESIS; TERMINAL ALKYNES; H ACTIVATION; ALKALOIDS;

D O I：

10.1039/c4cc04555f

中图分类号：

O6 [化学];

学科分类号：

070301 [无机化学];

摘要：

A facile regiospecific synthesis of 2,3-disubstituted indoles from isatins has been developed. Nucleophilic addition of Grignard reagents to commercially available isatins, followed by reduction with borane, afforded an array of structurally diverse 2,3-disubstituted indoles in moderate to good yields. The method described herein represents a novel and very simple approach to synthesize various 2,3-disubstituted indoles, extremely important structural motifs in the pharmaceutical industry and medicinal chemistry.

引用

收藏

页码：9469 / 9472

页数：4

相关论文

共 61 条

[1]

Alex K., 2008, ORG BIOMOL CHEM, V11, P2417

[2]

Zinc-promoted hydrohydrazination of terminal alkynes: An efficient domino synthesis of indoles [J].

Alex, Karolin ;

Tillack, Annegret ;

Schwarz, Nicolle ;

Beller, Matthias .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (12) :2304-2307

[3]

2-SUBSTITUTED-3-ACYLINDOLES THROUGH THE PALLADIUM-CATALYZED CARBONYLATIVE CYCLIZATION OF 2-ALKYNYLTRIFLUOROACETANILIDES WITH ARYL HALIDES AND VINYL TRIFLATES [J].

ARCADI, A ;

CACCHI, S ;

CARNICELLI, V ;

MARINELLI, F .

TETRAHEDRON, 1994, 50 (02) :437-452

[4]

Applications of Bartoli indole synthesis [J].

Bartoli, Giuseppe ;

Dalpozzo, Renato ;

Nardi, Monica .

CHEMICAL SOCIETY REVIEWS, 2014, 43 (13) :4728-4750

[5]

Copper-Catalyzed C-C Bond Formation through C-H Functionalization: Synthesis of Multisubstituted Indoles from N-Aryl Enaminones [J].

Bernini, Roberta ;

Fabrizi, Giancarlo ;

Sferrazza, Alessio ;

Cacchi, Sandro .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (43) :8078-8081

[6]

A Pd(0)-Mediated Indole (Macro)cyclization Reaction [J].

Breazzano, Steven P. ;

Poudel, Yam B. ;

Boger, Dale L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (04) :1600-1606

[7]

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

Cacchi, S ;

Fabrizi, G .

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

[8]

Update 1 of: Synthesis and Functionalization of Indoles Through Palladium-Catalyzed Reactions [J].

Cacchi, Sandro ;

Fabrizi, Giancarlo .

CHEMICAL REVIEWS, 2011, 111 :PR215-PR283

[9]

2,3-Disubstituted Indoles via Palladium-Catalyzed Reaction of 2-Alkynyltrifluoroacetanilides with Arenediazonium Tetrafluoroborates [J].

Cacchi, Sandro ;

Fabrizi, Giancarlo ;

Goggiamani, Antonella ;

Perboni, Alcide ;

Sferrazza, Alessio ;

Stabile, Paolo .

ORGANIC LETTERS, 2010, 12 (14) :3279-3281

[10]

Intermolecular alkyne hydroaminations involving 1,1-disubstituted hydrazines [J].

Cao, CS ;

Shi, YH ;

Odom, AL .

ORGANIC LETTERS, 2002, 4 (17) :2853-2856

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