A Facile and Efficient One-Pot Synthesis of Substituted Quinolines from α-Arylamino Ketones Under Vilsmeier Conditions

被引：16

作者：

Wang, Yan ^{[1
,2
]}

Xin, Xin ^{[1
,2
]}

Liang, Yongjiu ^{[2
]}

Lin, Yingjie ^{[1
]}

Zhang, Rui ^{[2
]}

Dong, Dewen ^{[2
]}

机构：

[1] Jilin Univ, Dept Chem, Changchun 130023, Peoples R China

[2] Chinese Acad Sci, Changchun Inst Appl Chem, Changchun 130022, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 2009卷 / 24期

基金：

中国国家自然科学基金;

关键词：

Heterocycles; Cyclization; Aromatization; Amino ketones; Formylation; Vilsmeier-Haack reaction; ONE-STEP SYNTHESIS; DIETHYL CHLOROPHOSPHITE; CARBONYL-COMPOUNDS; RING-ENLARGEMENT; HAACK REACTIONS; QUINAZOLINE; SALTS; DERIVATIVES; CYCLIZATION; PYRIDINES;

D O I：

10.1002/ejoc.200900430

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient one-pot synthesis of substituted quinolines from alpha-arylamino ketones in the presence of PBr3 in DMF has been developed. This general protocol provides a novel and facile access to substituted quinolines by sequential Vilsmeier-Haack reaction, intramolecular cyclization and aromatization reactions of alpha-arylamino ketones. PBr3 plays a dual role in the quinoline synthesis: as a key component of the Vilsmeier reagent (PBr3/DMF) and as a reducing reagent. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

引用

页码：4165 / 4169

页数：5

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