Practical methodologies for the synthesis of indoles

被引：2061

作者：

Humphrey, Guy R. ^{[1
]}

Kuethe, Jeffrey T. ^{[1
]}

机构：

[1] Merck & Co Inc, Dept Proc Res, Rahway, NJ 07065 USA

来源：

CHEMICAL REVIEWS | 2006年 / 106卷 / 07期

关键词：

D O I：

10.1021/cr0505270

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

To synthetic chemists who design industrial or manufacturing syntheses as well as researchers in academia, the implementation of practical, safe, and scalable methods for the large-scale preparation of indoles is of critical interest. This review highlights the practical methodologies which have either been successfully demonstrated or are potentially useful for the large-scale synthesis of indoles. Reaction methodologies that have appeared in the scientific literature between 1995 and June 2005 are discussed with emphasis on those reactions leading to the indole ring.

引用

页码：2875 / 2911

页数：37

共 268 条

[71] Furo[3,4-b]furan formations from alkynols of xylose [J].

Djuardi, E ;

Mc Nelis, E .

TETRAHEDRON LETTERS, 1999, 40 (40) :7193-7196

[72] Synthesis of a fully functionalized 7-methoxyaziridinomitosene [J].

Dong, WT ;

Jimenez, LS .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07) :2520-2523

[73] Indoles from o-haloanilines: Syntheses of tryptamines and tryptophols via regioselective hydroformylation of functionalized anilines [J].

Dong, Y ;

Busacca, CA .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (19) :6464-6465

[74] The asymmetric intramolecular Heck reaction in natural product total synthesis [J].

Dounay, AB ;

Overman, LE .

CHEMICAL REVIEWS, 2003, 103 (08) :2945-2963

[75] BULKY METAL ARYLOXIDES, ARYLAMIDES, AND SULFUR AND PHOSPHORUS ANALOGS .1. SYNTHETIC AND CHEMICAL STUDIES OF TITANIUM AND ZIRCONIUM ARYLOXIDES [J].

DUFF, AW ;

KAMARUDIN, RA ;

LAPPERT, MF ;

NORTON, RJ .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1986, (03) :489-498

[76] Practical alternatives for the synthesis of β-iodofurans by 5-endo-dig cyclisations of 3-alkyne-1,2-diols [J].

El-Taeb, GMM ;

Evans, AB ;

Jones, S ;

Knight, DW .

TETRAHEDRON LETTERS, 2001, 42 (34) :5945-5948

[77] Synthesis and cross-coupling reactions of substituted 5-triflyloxyindoles [J].

England, DB ;

Kerr, MA .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16) :6519-6522

[78] METHODS FOR DRUG DISCOVERY - DEVELOPMENT OF POTENT, SELECTIVE, ORALLY EFFECTIVE CHOLECYSTOKININ ANTAGONISTS [J].

EVANS, BE ;

RITTLE, KE ;

BOCK, MG ;

DIPARDO, RM ;

FREIDINGER, RM ;

WHITTER, WL ;

LUNDELL, GF ;

VEBER, DF ;

ANDERSON, PS ;

CHANG, RSL ;

LOTTI, VJ ;

CERINO, DJ ;

CHEN, TB ;

KLING, PJ ;

KUNKEL, KA ;

SPRINGER, JP ;

HIRSHFIELD, J .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (12) :2235-2246

[79] Efficient reagents for the synthesis of 5-, 7-, and 5,7-substituted indoles starting from aromatic amines: Scope and limitations [J].

Ezquerra, J ;

Pedregal, C ;

Lamas, C ;

Barluenga, J ;

Perez, M ;

GarciaMartin, MA ;

Gonzalez, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (17) :5804-5812

[80] Solid-phase synthesis of indoles using the palladium-catalysed coupling of alkynes with iodoaniline derivatives. [J].

Fagnola, MC ;

Candiani, I ;

Visentin, G ;

Cabri, W ;

Zarini, F ;

Mongelli, N ;

Bedeschi, A .

TETRAHEDRON LETTERS, 1997, 38 (13) :2307-2310

← 3 4 5 6 7 8 9 10 11 12 →