Efficient construction of indole rings from 2-ethynylaniline derivatives catalyzed by copper(II) salts and its application to the tandem cyclization reactions

被引：111

作者：

Hiroya, K ^{[1
]}

Itoh, S ^{[1
]}

Ozawa, M ^{[1
]}

Kanamori, Y ^{[1
]}

Sakamoto, T ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Aoba Ku, Sendai, Miyagi 9808578, Japan

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 07期

关键词：

indole; cyclization reaction; copper(II) trifluoromethanesulfonate; copper(II) acetate; 2-ethynylaniline;

D O I：

10.1016/S0040-4039(01)02396-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The efficient cyclization reactions of the N-methanesulfonyl or N-ethoxycarbonyl derivatives of 2-ethynylanilines. functionalized on the benzene ring and/or the acetylene terminal into indoles catalyzed by either Cu(OTf)(2) or Cu(OAc)(2) are accomplished. The application of this reaction to the tandem cyclization reaction is also described. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：1277 / 1280

页数：4

共 25 条

[1] 2-SUBSTITUTED-3-ACYLINDOLES THROUGH THE PALLADIUM-CATALYZED CARBONYLATIVE CYCLIZATION OF 2-ALKYNYLTRIFLUOROACETANILIDES WITH ARYL HALIDES AND VINYL TRIFLATES [J].

ARCADI, A ;

CACCHI, S ;

CARNICELLI, V ;

MARINELLI, F .

TETRAHEDRON, 1994, 50 (02) :437-452

[2] PALLADIUM-CATALYZED COUPLING OF ARYL AND VINYL TRIFLATES OR HALIDES WITH 2-ETHYNYLANILINE - AN EFFICIENT ROUTE TO FUNCTIONALIZED 2-SUBSTITUTED INDOLES [J].

ARCADI, A ;

CACCHI, S ;

MARINELLI, F .

TETRAHEDRON LETTERS, 1989, 30 (19) :2581-2584

[3]

Cacchi S, 1999, SYNLETT, P620

[4] PALLADIUM-CATALYZED CYCLIZATION OF 2-ALKYNYLANILINES TO 2-SUBSTITUTED INDOLES UNDER AN ACIDIC 2-PHASE SYSTEM [J].

CACCHI, S ;

CARNICELLI, V ;

MARINELLI, F .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1994, 475 (1-2) :289-296

[5]

Cacchi S, 1997, SYNLETT, P1363

[6] Palladium-catalyzed cyclization of o-alkynyltrifluoroacetanilides with allyl esters. A regioselective synthesis of 3-allylindoles [J].

Cacchi, S ;

Fabrizi, G ;

Pace, P .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (04) :1001-1011

[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] Recent developments in indole ring synthesis-methodology and applications [J].

Gribble, GW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (07) :1045-1075

[9]

GRIBBLE GW, 1996, COMPREHENSIVE HETERO, V2, P207, DOI DOI 10.1016/B978-008096518-5.00043-5

[10] PALLADIUM CATALYZED REACTION OF 2-ALKYNYLANILINES WITH ALLYL CHLORIDES - FORMATION OF 3-ALLYLINDOLES [J].

IRITANI, K ;

MATSUBARA, S ;

UTIMOTO, K .

TETRAHEDRON LETTERS, 1988, 29 (15) :1799-1802

← 1 2 3 →