Synthesis of new tetrahydroquinoline and quinoline derivatives via the aza-Diels-Alder reaction with aromatization

被引：37

作者：

Fadel, F

Titouani, SL

Soufiaoui, M

Ajamay, H

Mazzah, A

机构：

[1] Univ Mohammed 5, Fac Sci, Associe CNCPRST, Lab Chim Plantes & Synth Organ & Bioorgan, Rabat, Morocco

[2] Univ Lille 1, UMR 8516, Lab Spectrochim Infrarouge & Ramon, F-59655 Villeneuve Dascq, France

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 30期

关键词：

aza-Diels-Alder; tetrahydroquinoline; quinoline;

D O I：

10.1016/j.tetlet.2004.05.127

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Aza-Diels-Alder reaction of aldimines with isoeugenol is described. New 1, 2,3,4-tetrahydroquinoline and quinoline structures are reported. The stereo- and regioselectivities of the [4+2] cycloaddition are discussed. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：5905 / 5908

页数：4

共 34 条

[1] Indium trichloride (InCl3)catalyzed imino Diels-Alder reactions:: An efficient synthesis of cyclopentaquinolines, azabicyclooctanones and azabicyclononanones.
Babu, G
Perumal, PT
[J]. TETRAHEDRON, 1998, 54 (08) : 1627 - 1638
[2] Parallel synthesis of polysubstituted tetrahydroquinolines
Baudelle, R
Melnyk, P
Déprez, B
Tartar, A
[J]. TETRAHEDRON, 1998, 54 (16) : 4125 - 4140
[3] Diels-Alder reactions of 1-azadienes
Behforouz, M
Ahmadian, M
[J]. TETRAHEDRON, 2000, 56 (30) : 5259 - 5288
[4] DIELS-ALDER REACTIONS OF AZADIENES
BOGER, DL
[J]. TETRAHEDRON, 1983, 39 (18) : 2869 - 2939
[5] BOGER DL, 1987, HETERO DIELS ALDER M, P71
[6] BOGER DL, 1990, COMPREHENSIVE ORGANI, V5
[7] Recent developments in imino Diels-Alder reactions
Buonora, P
Olsen, JC
Oh, T
[J]. TETRAHEDRON, 2001, 57 (29) : 6099 - 6138
[8] SCHIZOID REACTIVITY OF N-BENZYLIDENE ANILINE TOWARD CLAY-CATALYZED CYCLO-ADDITIONS
CABRAL, J
LASZLO, P
MONTAUFIER, MT
[J]. TETRAHEDRON LETTERS, 1988, 29 (05) : 547 - 550
[9] PRODUCT DISTRIBUTION IN DIELS-ALDER ADDITION OF N-BENZYLIDENE ANILINE ANILINE AND ENOL ETHERS
CABRAL, J
LASZLO, P
[J]. TETRAHEDRON LETTERS, 1989, 30 (51) : 7237 - 7238
[10] ANTICONVULSANT ACTIVITY OF GLYCINE-SITE NMDA ANTAGONISTS .2. TRANS 2-CARBOXY-4-SUBSTITUTED TETRAHYDROQUINOLINES
CARLING, RW
LEESON, PD
MOSELEY, AM
SMITH, JD
SAYWELL, K
TRICKLEBANK, MD
KEMP, JA
MARSHALL, GR
FOSTER, AC
GRIMWOOD, S
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (01) : 65 - 70

← 1 2 3 4 →