Hg(OTf)2-catalyzed cycloisomerization of 2-ethynylaniline derivatives leading to indoles

被引：64

作者：

Kurisaki, Takahiro ^{[1
]}

Naniwa, Tomoko ^{[1
]}

Yamamoto, Hirofumi ^{[1
]}

Imagawa, Hiroshi ^{[1
]}

Nishizawa, Mugio ^{[1
]}

机构：

[1] Tokushima Bunri Univ, Fac Pharmaceut Sci, Tokushima 7708514, Japan

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 10期

关键词：

D O I：

10.1016/j.tetlet.2006.12.120

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cycloisomerization of 2-ethynylaniline derivatives catalyzed by mercuric triflate afforded indole derivatives in excellent yield under mild reaction conditions with high catalytic turnover up to 100 times. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：1871 / 1874

页数：4

共 60 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] IPy2BF4-promoted intramolecular addition of masked and unmasked anilines to alkynes:: Direct assembly of 3-iodoindole cores [J].

Barluenga, J ;

Trincado, M ;

Rubio, E ;

González, JM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (21) :2406-2409

[4]

Battistuzzi G, 2002, EUR J ORG CHEM, V2002, P2671

[5] 2-aryl and 2-heteroaryl indoles from 1-alkynes and o-lodotrifluoroacetanilide through a domino copper-catalyzed coupling-cyclization process [J].

Cacchi, S ;

Fabrizi, G ;

Parisi, LM .

ORGANIC LETTERS, 2003, 5 (21) :3843-3846

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

CASTRO, CE ;

GAUGHAN, EJ ;

OWSLEY, DC .

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

[8] Microwave-assisted solid-phase organic synthesis (MASPOS) as a key step for an indole library construction [J].

Dai, WM ;

Guo, DS ;

Sun, LP ;

Huang, XH .

ORGANIC LETTERS, 2003, 5 (16) :2919-2922

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

Dai, WM ;

Sun, LP ;

Guo, DS .

TETRAHEDRON LETTERS, 2002, 43 (43) :7699-7702

[10] 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

← 1 2 3 4 5 6 →