Ruthenium-catalyzed heteroannulation of anilines with alkanolammonium chlorides leading to indoles

被引：67

作者：

Cho, CS ^{[1
]}

Kim, JH ^{[1
]}

Kim, TJ ^{[1
]}

Shim, SC ^{[1
]}

机构：

[1] Kyungpook Natl Univ, Coll Engn, Dept Ind Chem, Taegu 702701, South Korea

来源：

TETRAHEDRON | 2001年 / 57卷 / 16期

关键词：

amine exchange reaction; aqueous medium; catalyst; heteroannulation; indoles; ruthenium;

D O I：

10.1016/S0040-4020(01)00202-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Anilines react with alkanolammonium chlorides in an aqueous medium (H2O-dioxane) at 180 degreesC in the presence of a catalytic amount of a ruthenium catalyst together with SnCl2. 2H(2)O to afford the corresponding indoles in moderate to good yields. Especially, when triisopropanolammonium chloride is employed to react with anilines, 2-methylindoles are formed regioselectively. The presence of SnCl2. 2H(2)O is necessary for the effective formation of indoles. A reaction pathway involving alkanol group transfer from alkanolamines to anilines, N-alkylation of anilines by anilinoalkanols and heteroannulation of 1,2-dianilinoalkanes is proposed for this catalytic process. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：3321 / 3329

页数：9

共 78 条

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