Ruthenium-catalyzed regioselective synthesis of 2-substituted indoles via ring-opening of epoxides by anilines

被引：30

作者：

Cho, CS ^{[1
]}

Kim, JH

Choi, HJ

Kim, TJ

Shim, SC

机构：

[1] Kyungpook Natl Univ, Ind Technol Res Inst, Taegu 702701, South Korea

[2] Kyungpook Natl Univ, Dept Ind Chem, Taegu 702701, South Korea

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 14期

基金：

新加坡国家研究基金会;

关键词：

anilines; epoxides; indoles; ring-opening; ruthenium catalyst;

D O I：

10.1016/S0040-4039(03)00396-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Anilines react with epoxides in dioxane at 180degreesC in the presence of a catalytic amount of a ruthenium catalyst along with tin(II) chloride to afford 2-substituted indoles in moderate to good yields. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：2975 / 2977

页数：3

共 26 条

[11]

Cho CS, 2001, ANGEW CHEM INT EDIT, V40, P958, DOI 10.1002/1521-3773(20010302)40:5<958::AID-ANIE958>3.0.CO

[12]

2-4

[13] Ruthenium-catalyzed synthesis of 2-ethyl-3-methylquinolines from anilines and triallylamine [J].

Cho, CS ;

Oh, BH ;

Shim, SC .

TETRAHEDRON LETTERS, 1999, 40 (08) :1499-1500

[14] TRANSITION-METALS IN THE SYNTHESIS AND FUNCTIONALIZATION OF INDOLES [J].

HEGEDUS, LS .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (09) :1113-1226

[15] TRANSITION-METAL TIN CHEMISTRY [J].

HOLT, MS ;

WILSON, WL ;

NELSON, JH .

CHEMICAL REVIEWS, 1989, 89 (01) :11-49

[16] ONE-POT SYNTHESIS OF 3-ALKYLINDOLES FROM ORTHO-TOLYL ISOCYANIDES [J].

ITO, Y ;

KOBAYASHI, K ;

SEKO, N ;

SAEGUSA, T .

CHEMISTRY LETTERS, 1979, (10) :1273-1276

[17] SYNTHETIC ASPECTS OF METAL-CATALYZED OXIDATIONS OF AMINES AND RELATED REACTIONS [J].

MURAHASHI, SI .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (22) :2443-2465

[18] SYNTHESIS OF 1-SUBSTITUTED INDOLES BY THE VAPOR-PHASE REACTION OF N-SUBSTITUTED ANILINES WITH GLYCOLS AND EPOXIDES OVER A SOLID CATALYST AND A VAPOR-PHASE DEALKYLATION OF 1-ALKYLINDOLE [J].

NISHIDA, T ;

TOKUDA, Y ;

TSUCHIYA, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1995, (04) :823-830

[19] An efficient method for the ring opening of epoxides with aromatic amines catalyzed by bismuth trichloride [J].

Ollevier, T ;

Lavie-Compin, G .

TETRAHEDRON LETTERS, 2002, 43 (44) :7891-7893

[20]

REMERS WA, 1979, INDOLES, V25

← 1 2 3 →