Three-component coupling reactions of isoquinolines, dimethyl acetylenedicarboxylate and indoles: a facile synthesis of 3-indolyl-1, 2-dihydro-2-isoquinolinyl-2-butenedioate

被引：46

作者：

Yadav, J. S. ^{[1
]}

Reddy, B. V. Subba ^{[1
]}

Yadav, Nagendra Nath ^{[1
]}

Gupta, Manoj K. ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Div Organ Chem, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 17期

关键词：

isoquinoline/quinoline; indole; dimethyl acetylenedicarboxylate; 3-indolyl-dihydroisoquinolines;

D O I：

10.1016/j.tetlet.2008.02.129

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A three-component coupling of isoquinolines, dimethyl acetylenedicarboxylate (DMAD) and indoles is achieved for the first time to produce dimethyl (E_-2-[1-(1H-3-indolyl)-1,2-dihydro-2-isoquinolinyl]-2-butenedioates in excellent yields and with high selectivity. The reaction proceeds smoothly at room temperature without a catalyst. Quinoline, DMAD and indole also undergo smooth coupling to furnish dimethyl (E)-2-[2-(1H-3-indolyl)-1,2-dihydro-1-quinolinyl]-2-butenedioate under similar conditions. This method is very useful to functionalize both indoles and aza-aromatic compounds in a one-pot operation. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：2815 / 2819

页数：5

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