Copper-catalyzed cascade addition route to 2,3,4-trisubstituted quinoline derivatives

被引：13

作者：

Crifar, Cynthia ^{[1
]}

Doerr, Aurelie A. ^{[1
]}

Lubell, William D. ^{[1
]}

机构：

[1] Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 23期

基金：

加拿大自然科学与工程研究理事会;

关键词：

Quinolines; Copper-catalyzed cascade; Friedlander condensation; Anthranilate; Solvent-free synthesis; VINYL GRIGNARD-REAGENT; ONE-POT SYNTHESIS; ALKYNYLATION-CYCLIZATION; HOMOALLYLIC KETONES; EFFICIENT SYNTHESIS; DISCOVERY; AMIDE; ANALOGS; SERIES;

D O I：

10.1016/j.tetlet.2015.01.071

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In honor of the memory of Professor Harry H. Wassermann, we present the synthesis of various substituted quinolines. The copper-catalyzed cascade addition of vinylmagnesium bromide on methyl anthranilate (1) provided quantitatively 1-[2-aminophenyl]pent-4-en-1-one (2). Although attempts to annulate the pyridine ring on this o-acyl aniline using transition metal catalysis with acetylenes were unsuccessful, a one-pot, solvent-free Friedlander synthesis provided 8 quinolines. In light of the potential for the double bond to serve in diversification chemistry as well as the importance of 4-substituted quinolines, this method offers effective access to a valuable class of medicinally relevant targets. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：3451 / 3453

页数：3

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