An efficient protocol for the liquid-phase synthesis of furanoquinolines and pyranoquinolines

被引：35

作者：

Wang, YG ^{[1
]}

Lin, XF ^{[1
]}

Cui, SJ ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China

来源：

SYNLETT | 2004年 / 07期

关键词：

tetrahydroquinolines; quinolines; liquid-phase synthesis; polyethylene glycol (PEG);

D O I：

10.1055/s-2004-822913

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A three-step liquid-phase protocol for the synthesis of furanoquinolines and pyranoquinolines is described. The one-pot three-component aza-Diels-Alder reaction of PEG-supported benzaldehyde, anilines and 2,3-dihydrofuran or dihydropyran under TFA gave PEG-supported tetrahydroquinolines, which was assuredly oxidized by DDQ and then cleaved from the support to afford the corresponding furanoquinolines and pyranoquinolines with reasonable yields and purity.

引用

页码：1175 / 1178

页数：4

共 31 条

[1]

ALEXANDER SK, 1998, TETRAHEDRON, V54, P7987

[2]

ALEXANDER SK, 1997, TETRAHEDRON LETT, V35, P6163

[3]

Annunziata R, 2000, CHEM-EUR J, V6, P133, DOI 10.1002/(SICI)1521-3765(20000103)6:1<133::AID-CHEM133>3.0.CO

[4]

2-H

[5]

Blettner CG, 1999, SYNLETT, P307

[6]

Boger D.L., 1987, HETERO DIELS ALDER M

[7]

Boger D. L., 1987, HETERO DIELS ALDER M

[8] Diastereoselective synthesis of substituted tetrahydroquinoline-4-carboxylic esters by a tandem reduction-reductive amination reaction [J].

Bunce, RA ;

Herron, DM ;

Johnson, LB ;

Kotturi, SV .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (08) :2822-2827

[9] Organic synthesis on soluble polymer supports: Liquid-phase methodologies [J].

Gravert, DJ ;

Janda, KD .

CHEMICAL REVIEWS, 1997, 97 (02) :489-509

[10] Liquid-phase synthesis of 2,3-dihydro-4-pyridones: one-pot three-component aza Diels-Alder reaction of Danishefsky's diene with aldehydes and PEG-supported amine [J].

Guo, HC ;

Ding, KL .

TETRAHEDRON LETTERS, 2003, 44 (37) :7103-7106

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