New vistas in quinoline synthesis

被引：87

作者：

Atechian, Sarkis ^{[1
]}

Nock, Nadine ^{[1
]}

Norcross, Roger D. ^{[1
]}

Ratni, Hassen ^{[1
]}

Thomas, Andrew W. ^{[1
]}

Verron, Julien ^{[1
]}

Masciadri, Raffaello ^{[1
]}

机构：

[1] F Hoffmann La Roche Ltd, Div Pharmaceut, Discovery Chem, CH-4070 Basel, Switzerland

来源：

TETRAHEDRON | 2007年 / 63卷 / 13期

关键词：

sodium tetrachloroaurate; gold-catalyzed Friedlander reaction; regioselectivity; 3-(methanesulfonyl)quinolines; Sugasawa reaction; gallium chloride;

D O I：

10.1016/j.tet.2007.01.050

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The gold-catalyzed Friedlander reaction was applied to the condensation of 2-aminoarylketones with beta-keto-esters, beta-diketones, beta-keto-amides, and beta-keto-sulfones to afford a diverse range of 2,3,4-trisubstituted quinolines in 3-82% yield. The seven-membered rings 1,3-cycloheptadione and azepane-2,4-dione reacted smoothly in 75% yield. An alternative procedure for the synthesis of 3-(methanesulfonyl)quinolines was developed and provided an entry into late stage manipulation of the 4-position of these quinolines. The requisite 2-aminoarylketones for the Friedlander reaction were prepared in one pot by modified Sugasawa reaction using gallium(111) chloride and boron(III) chloride in 12-54% yield. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：2811 / 2823

页数：13

共 28 条

[1] An improved method for the palladium-catalyzed amination of aryl iodides [J].

Ali, MH ;

Buchwald, SL .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (08) :2560-2565

[2] Palladium-catalyzed amination of aryl nonaflates [J].

Anderson, KW ;

Mendez-Perez, M ;

Priego, J ;

Buchwald, SL .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (25) :9563-9573

[3] A new green approach to the Friedlander synthesis of quinolines [J].

Arcadi, A ;

Chiarini, M ;

Di Giuseppe, S ;

Marinelli, F .

SYNLETT, 2003, (02) :203-206

[4]

Borsche W, 1939, LIEBIGS ANN CHEM, V538, P283

[5]

CHENG CC, 1982, ORG REACTIONS, V28, P37

[6] 4-HYDROXY-3-QUINOLINECARBOXAMIDES WITH ANTIARTHRITIC AND ANALGESIC ACTIVITIES [J].

CLEMENCE, F ;

LEMARTRET, O ;

DELEVALLEE, F ;

BENZONI, J ;

JOUANEN, A ;

JOUQUEY, S ;

MOUREN, M ;

DERAEDT, R .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (07) :1453-1462

[7] The first total synthesis of the proposed structure of Montiporyne E [J].

Collison, Christina G. ;

Chen, Jian ;

Walvoord, Ryan .

SYNTHESIS-STUTTGART, 2006, (14) :2319-2322

[8] Reactions of 2-methyl-3,1-benzoxazin-4-one with active methylene compounds: A new route to 3-substituted 4-hydroxyquinolin-2(1H)-ones [J].

Detsi, A ;

Bardakos, V ;

Markopoulos, J ;

IgglessiMarkopoulou, O .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (24) :2909-2913

[9] IN-SITU NMR SPECTROSCOPIC STUDIES OF ANILINE ORTHO ACYLATION (SUGASAWA REACTION) - THE NATURE OF REACTION INTERMEDIATES AND LEWIS-ACID INFLUENCE ON YIELD [J].

DOUGLAS, AW ;

ABRAMSON, NL ;

HOUPIS, IN ;

KARADY, S ;

MOLINA, A ;

XAVIER, LC ;

YASUDA, N .

TETRAHEDRON LETTERS, 1994, 35 (37) :6807-6810

[10] FRIEDLANDER SYNTHESES WITH O-AMINOARYL KETONES .2. STRUCTURE OF PRODUCT FORMED IN CONDENSATION OF O-AMINOBENZOPHENONE WITH ACETYLACETONE [J].

FEHNEL, EA ;

COHN, DE .

JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (11) :3852-&

← 1 2 3 →