A copper(II)-catalyzed protocol for modified Friedländer quinoline synthesis

Chan Sik Cho; Wen Xiu Ren; Sang Chul Shim

doi:10.1016/j.tetlet.2006.07.067

A copper(II)-catalyzed protocol for modified Friedländer quinoline synthesis

Chan Sik Cho, Wen Xiu Ren, Sang Chul Shim

Department of Applied Chemistry

Kyungpook National University

Research output: Contribution to journal › Article › peer-review

78 Scopus citations

Abstract

2-Aminobenzyl alcohol reacts with an array of ketones in dioxane at 100 °C in the presence of a catalytic amount of CuCl₂ along with KOH under O₂ atmosphere to afford the corresponding quinolines in good yields. 2-Aminobenzyl alcohol is also oxidatively coupled and cyclized with various aldehydes by step-by-step procedure, an initial treatment of 2-aminobenzyl alcohol in the presence of CuCl₂ and KOH in dioxane under O₂ atmosphere and subsequent addition of aldehyde to the mixture followed by stirring under argon atmosphere, to give 3-substituted quinolines in moderate to good yields.

Original language	English
Pages (from-to)	6781-6785
Number of pages	5
Journal	Tetrahedron Letters
Volume	47
Issue number	38
DOIs	https://doi.org/10.1016/j.tetlet.2006.07.067
State	Published - 18 Sep 2006

Keywords

2-Aminobenzyl alcohol
Aldehydes
Copper catalyst
Ketones
Quinolines

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10.1016/j.tetlet.2006.07.067

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title = "A copper(II)-catalyzed protocol for modified Friedl{\"a}nder quinoline synthesis",

abstract = "2-Aminobenzyl alcohol reacts with an array of ketones in dioxane at 100 °C in the presence of a catalytic amount of CuCl2 along with KOH under O2 atmosphere to afford the corresponding quinolines in good yields. 2-Aminobenzyl alcohol is also oxidatively coupled and cyclized with various aldehydes by step-by-step procedure, an initial treatment of 2-aminobenzyl alcohol in the presence of CuCl2 and KOH in dioxane under O2 atmosphere and subsequent addition of aldehyde to the mixture followed by stirring under argon atmosphere, to give 3-substituted quinolines in moderate to good yields.",

keywords = "2-Aminobenzyl alcohol, Aldehydes, Copper catalyst, Ketones, Quinolines",

author = "Cho, {Chan Sik} and Ren, {Wen Xiu} and Shim, {Sang Chul}",

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T1 - A copper(II)-catalyzed protocol for modified Friedländer quinoline synthesis

AU - Cho, Chan Sik

AU - Ren, Wen Xiu

AU - Shim, Sang Chul

PY - 2006/9/18

Y1 - 2006/9/18

N2 - 2-Aminobenzyl alcohol reacts with an array of ketones in dioxane at 100 °C in the presence of a catalytic amount of CuCl2 along with KOH under O2 atmosphere to afford the corresponding quinolines in good yields. 2-Aminobenzyl alcohol is also oxidatively coupled and cyclized with various aldehydes by step-by-step procedure, an initial treatment of 2-aminobenzyl alcohol in the presence of CuCl2 and KOH in dioxane under O2 atmosphere and subsequent addition of aldehyde to the mixture followed by stirring under argon atmosphere, to give 3-substituted quinolines in moderate to good yields.

AB - 2-Aminobenzyl alcohol reacts with an array of ketones in dioxane at 100 °C in the presence of a catalytic amount of CuCl2 along with KOH under O2 atmosphere to afford the corresponding quinolines in good yields. 2-Aminobenzyl alcohol is also oxidatively coupled and cyclized with various aldehydes by step-by-step procedure, an initial treatment of 2-aminobenzyl alcohol in the presence of CuCl2 and KOH in dioxane under O2 atmosphere and subsequent addition of aldehyde to the mixture followed by stirring under argon atmosphere, to give 3-substituted quinolines in moderate to good yields.

KW - 2-Aminobenzyl alcohol

KW - Aldehydes

KW - Copper catalyst

KW - Ketones

KW - Quinolines

UR - http://www.scopus.com/inward/record.url?scp=33747158781&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2006.07.067

DO - 10.1016/j.tetlet.2006.07.067

M3 - Article

AN - SCOPUS:33747158781

SN - 0040-4039

VL - 47

SP - 6781

EP - 6785

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 38

ER -

A copper(II)-catalyzed protocol for modified Friedländer quinoline synthesis

Abstract

Keywords

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