Chemistry of aminophenols. Part 2: A general and efficient synthesis of indoles possessing a nitrogen substituent at the C4, C5, C6, and C7 positions

被引：55

作者：

Dai, WM ^{[1
]}

Sun, LP

Guo, DS

机构：

[1] Hong Kong Univ Sci & Technol, Combinatorial Chem Lab, Kowloon, Hong Kong, Peoples R China

[2] Hong Kong Univ Sci & Technol, Biotechnol Res Inst, Kowloon, Hong Kong, Peoples R China

[3] Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Hong Kong, Peoples R China

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 43期

关键词：

coupling reactions; indoles; phenols; triflates;

D O I：

10.1016/S0040-4039(02)01851-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general and efficient synthesis of indoles possessing a nitrogen substituent at the C4, C5, C6, and C7 positions has been developed. Starting from commercially available nitro 2-aminophenols, 5-, 6-, and 7-arenesulfamoylindoles were synthesized via a base-promoted ring closure of 2-alkynylanilides, reduction of the nitro group, and sulfonylation. C4 nitrogen substituted indoles, were synthesized from 2-chloro- 1,3-dinitrobenzene via cyclization of 2-alkynyl- 1,3-diaminobenzene as the key step. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：7699 / 7702

页数：4

共 21 条

[1] Leukotriene modulators as therapeutic agents in asthma and other inflammatory diseases [J].

Bell, RL ;

Summers, JB ;

Harris, RR .

ANNUAL REPORTS IN MEDICINAL CHEMISTRY, VOL 32, 1997, 32 :91-100

[2] SELECTIVE REDUCTION OF AROMATIC NITRO-COMPOUNDS WITH STANNOUS CHLORIDE IN NON-ACIDIC AND NON-AQUEOUS MEDIUM [J].

BELLAMY, FD ;

OU, K .

TETRAHEDRON LETTERS, 1984, 25 (08) :839-842

[3] INDOLES BENZOFURANS PHTHALIDES AND TOLANES VIA COPPER(1) ACETYLIDES [J].

CASTRO, CE ;

GAUGHAN, EJ ;

OWSLEY, DC .

JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (12) :4071-+

[4] Stereoselective synthesis of (Z)-ketoeneynes via Pd(0)-Cu(I)-catalyzed cross-coupling of (Z)-ketoenol triflate with 1-alkynes [J].

Dai, WM ;

Wu, JL .

TETRAHEDRON, 1997, 53 (27) :9107-9114

[5] HIGHLY CHEMOSELECTIVE ACYLATION OF SUBSTITUTED AMINOPHENOLS WITH 3-(TRIMETHYLACETYL)-1,3-THIAZOLIDINE-2-THIONE [J].

DAI, WM ;

CHEUNG, YK ;

TANG, KW ;

CHOI, PY ;

CHUNG, SL .

TETRAHEDRON, 1995, 51 (45) :12263-12276

[6] Chemistry of aminophenols. Part 1: Remarkable additive effect on Sonogashira cross-coupling of 2-carboxamidoaryl triflates and application to novel synthesis of indoles [J].

Dai, WM ;

Guo, DS ;

Sun, LP .

TETRAHEDRON LETTERS, 2001, 42 (31) :5275-5278

[7] 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

[8] To market, to market - 1996 [J].

Galatsis, P .

ANNUAL REPORTS IN MEDICINAL CHEMISTRY, VOL 32, 1997, 32 :305-326

[9] Pd(PhCN)2Cl2/P(t-Bu)3:: A versatile catalyst for sonogashira reactions of aryl bromides at room temperature [J].

Hundertmark, T ;

Littke, AF ;

Buchwald, SL ;

Fu, GC .

ORGANIC LETTERS, 2000, 2 (12) :1729-1731

[10] FACILE SYNTHESIS OF 2-SUBSTITUTED INDOLES AND INDOLO[3,2-B] CARBAZOLES FROM 2-(BENZOTRIAZOL-1-YLMETHYL)INDOLE [J].

KATRITZKY, AR ;

LI, JQ ;

STEVENS, CV .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (11) :3401-3404

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