Access to 4-substituted 3,4-dihydroquinolin-2(1H)-ones by an unusual radical cyclisation of a secondary amide

被引：33

作者：

Binot, G ^{[1
]}

Zard, SZ ^{[1
]}

机构：

[1] Ecole Polytech, Associe CNRS, Synth Organ Lab, F-91128 Palaiseau, France

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 44期

关键词：

3,4-dihydroquinolin-2(1H)-ones; xanthates; radical cyclisation;

D O I：

10.1016/j.tetlet.2005.09.006

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel route to 3,4-dihydroquinolin-2(1H)-ones involving two radical addition steps is reported, starting from readily accessible xanthates and N-aryl-3-butenamides. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：7503 / 7506

页数：4

共 20 条

[1] A formal synthesis of (±) parvifoline by manganese(III)-based oxidative arylation of ketones [J].

Bhowmik, DR ;

Venkateswaran, RV .

TETRAHEDRON LETTERS, 1999, 40 (41) :7431-7433

[2]

Binot G, 2003, SYNLETT, P382

[3] A convergent synthesis of 4-substituted 1,2,3,4-tetrahydroisoquinolin-1-ones [J].

Cholleton, N ;

Zard, SZ .

TETRAHEDRON LETTERS, 1998, 39 (40) :7295-7298

[4] Synthesis of five-, six-, and seven-membered ring lactams by Cp*Rh complex-catalyzed oxidative N-heterocyclization of amino alcohols [J].

Fujita, K ;

Takahashi, Y ;

Owaki, M ;

Yamamoto, K ;

Yamaguchi, R .

ORGANIC LETTERS, 2004, 6 (16) :2785-2788

[5] Total synthesis of cavicularin and riccardin C: Addressing the synthesis of an arene that adopts a boat configuration [J].

Harrowven, DC ;

Woodcock, T ;

Howes, PD .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (25) :3899-3901

[6]

Jones G., 1984, COMPREHENSIVE HETERO, V2

[7]

Jones G., 1996, Elsevier, V5, P167

[8] Synthesis of 2-quinolones via palladium-catalyzed carbonylative annulation of internal alkynes by N-substituted o-iodoanilines [J].

Kadnikov, DV ;

Larock, RC .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (20) :6772-6780

[9] Trifluoroacetic acid-mediated hydroarylation: Synthesis of dihydrocoumarins and dihydroquinolones [J].

Li, K ;

Foresee, LN ;

Tunge, JA .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (07) :2881-2883

[10] The importance of fluorine in the life science industry [J].

Maienfisch, P ;

Hall, RG .

CHIMIA, 2004, 58 (03) :93-99

← 1 2 →