Synthesis of N-substituted indole derivatives via PIFA-mediated intramolecular cyclization

被引：184

作者：

Du, Yunfei ^{[1
]}

Liu, Renhe ^{[1
]}

Linn, Gregory ^{[1
]}

Zhao, Kang ^{[1
]}

机构：

[1] Tianjin Univ, Coll Pharmaceut & Biotechnol, Tianjin 300072, Peoples R China

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 26期

关键词：

D O I：

10.1021/ol062288o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of N- arylated and N- alkylated indole derivatives were synthesized by way of a phenyliodine bis( trifluoroacetate) ( PIFA)- mediated intramolecular cyclization. This novel method allows for the construction of an indole skeleton by joining the N- atom on the side chain to the benzene ring at the last synthetic step. Other novel pyrrole- fused aromatic compounds can also be achieved by this method.

引用

页码：5919 / 5922

页数：4

共 40 条

[1] General and efficient indole syntheses based on catalytic amination reactions [J].

Ackermann, L .

ORGANIC LETTERS, 2005, 7 (03) :439-442

[2] OXIDATIVE RADICAL CYCLIZATION OF (OMEGA-IODOALKYL)INDOLES AND PYRROLES - SYNTHESIS OF (-)-MONOMORINE AND 3 DIASTEREOMERS [J].

ARTIS, DR ;

CHO, IS ;

JAIMEFIGUEROA, S ;

MUCHOWSKI, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (09) :2456-2466

[3] Synthesis of N-aryl indole-2-carboxylates via an intramolecular palladium-catalysed annulation of didehydrophenylalanine derivatives [J].

Brown, JA .

TETRAHEDRON LETTERS, 2000, 41 (10) :1623-1626

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

Cacchi, S ;

Fabrizi, G .

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

[5] Lewis acid-catalyzed synthesis of aziridines [J].

Casarrubios, L ;

Perez, JA ;

Brookhart, M ;

Templeton, JL .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (24) :8358-8359

[6] Optimization of 3-phenylpyrazolo[1,5-a[pyrimidines as potent corticotropin-releasing factor-1 antagonists with adequate lipophilicity and water solubility [J].

Chen, C ;

Wilcoxen, KM ;

Huang, CQ ;

McCarthy, JR ;

Chen, T ;

Grigoriadis, DE .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (14) :3669-3673

[7] Novel alternative for the N-N bond formation through a PIFA-mediated oxidative cyclization and its application to the synthesis of indazol-3-ones [J].

Correa, A ;

Tellitu, I ;

Dominguez, E ;

SanMartin, R .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (09) :3501-3505

[8] An alternative approach towards novel heterocycle-fused 1,4-diazepin-2-ones by an aromatic amidation protocol [J].

Correa, A ;

Herrero, MT ;

Tellitu, I ;

Domínguez, E ;

Moreno, I ;

SanMartin, R .

TETRAHEDRON, 2003, 59 (36) :7103-7110

[9] [1 + 4] CYCLOADDITION OF ISOCYANIDES WITH 1-ARYL-2-NITRO-1-PROPENES, METHYL 2-NITRO-3-ARYLPROPENOATES, AND METHYL 2-NITRO-2,4-PENTADIENOATES - SYNTHESIS OF 1-HYDROXYINDOLES AND 1-HYDROXYPYRROLES [J].

FOUCAUD, A ;

RAZORILALANARABEARIVONY, C ;

LOUKAKOU, E ;

PERSON, H .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (21) :3639-3644

[10] A NOVEL TIN-MEDIATED INDOLE SYNTHESIS [J].

FUKUYAMA, T ;

CHEN, XQ ;

PENG, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (07) :3127-3128

← 1 2 3 4 →