Synthesis of N-aryl indole-2-carboxylates via an intramolecular palladium-catalysed annulation of didehydrophenylalanine derivatives

被引：74

作者：

Brown, JA ^{[1
]}

机构：

[1] Celltech Chirosci PLC, Slough SL1 4EN, Berks, England

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 10期

关键词：

amination; Horner-Wadsworth-Emmons; indole-2-carboxylate; palladium catalysis;

D O I：

10.1016/S0040-4039(99)02344-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nitrogen substituted indole-2-carboxylates can be prepared via an intramolecular palladium-catalysed amination reaction of didehydrophenylalanine derivatives using PdCl2(dppf) and KOAc in DMF at 90 degrees C to form the indole nucleus. The specific formation of (Z)-isomers from Horner-Wadsworth-Emmons reaction of phosphonylglycinates and 2-iodobenzaldehydes was crucial to the success of the process, The product N-substituted indole-2-carboxylates were isolated in high yield. (C) 2000 Elsevier Science Ltd, Ail rights reserved.

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页码：1623 / 1626

页数：4

相关论文

共 14 条

[1] COPPER CATALYZED PHENYLATION OF INDOLES BY TRIPHENYLBISMUTH BIS-TRIFLUOROACETATE [J].

BARTON, DHR ;

FINET, JP ;

KHAMSI, J .

TETRAHEDRON LETTERS, 1988, 29 (10) :1115-1118

[2] METALLIC COPPER CATALYSIS OF N-ARYLATION OF AMINES BY TRIARYLBISMUTH DIACYLATES [J].

BARTON, DHR ;

FINET, JP ;

KHAMSI, J .

TETRAHEDRON LETTERS, 1986, 27 (31) :3615-3618

[3] 2-STEP SYNTHESIS OF SUBSTITUTED INDOLO[1,2-A]-QUINOXALIN-6-ONES [J].

BEACH, MJ ;

HOPE, R ;

KLAUBERT, DH ;

RUSSELL, RK .

SYNTHETIC COMMUNICATIONS, 1995, 25 (14) :2165-2183

[4]

Hartwig JF, 1998, ANGEW CHEM INT EDIT, V37, P2046, DOI 10.1002/(SICI)1521-3773(19980817)37:15<2046::AID-ANIE2046>3.0.CO

[5]

2-L

[6] Palladium-catalyzed amination of aryl halides: Mechanism and rational catalyst design [J].

Hartwig, JF .

SYNLETT, 1997, (04) :329-+

[7] FISCHER INDOLIZATION AND RELATED-COMPOUNDS .21. DIRECTION ON THE CYCLIZATION IN THE FISCHER INDOLIZATION OF ETHYL PYRUVATE 2-(PARA-SUBSTITUTED OR META-SUBSTITUTED PHENYL)PHENYLHYDRAZONES [J].

ISHII, H ;

TAKEDA, H ;

HAGIWARA, T ;

SAKAMOTO, M ;

KOGUSURI, K ;

MURAKAMI, Y .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (12) :2407-2414

[8]

ISHII H, 1990, CHEM PHARM BULL, V38, P2118

[9] An efficient copper-catalyzed coupling of aryl halides with imidazoles [J].

Kiyomori, A ;

Marcoux, JF ;

Buchwald, SL .

TETRAHEDRON LETTERS, 1999, 40 (14) :2657-2660

[10] NEW SYNTHETIC APPLICATIONS OF ARYLLEAD TRIACETATES - N-ARYLATION OF AZOLES [J].

LOPEZALVARADO, P ;

AVENDANO, C ;

MENENDEZ, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (17) :5678-5682