An efficient, high yielding protocol for the synthesis of functionalized quinolines via the tandem addition/annulation reaction of o-aminoaryl ketones with α-methylene ketones

被引：84

作者：

Bose, DS ^{[1
]}

Kumar, RK ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Organ Chem Div 3, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 05期

关键词：

2-aminoaryl ketones; alpha-methylene ketones; CeCl3.7H(2)O; Friedlander; quinolines;

D O I：

10.1016/j.tetlet.2005.11.075

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild and efficient method has been developed for the condensation of 2-aminoaryl ketones with alpha-methylene ketones in the presence of a catalytic amount of reusable catalyst CeCl(3)(.)7H(2)O (25 mol %) at ambient temperature to afford the corresponding poly-substituted quinolines in high yields under mild conditions. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：813 / 816

页数：4

共 37 条

[1] Electrochemical properties and electronic structures of conjugated polyquinolines and polyanthrazolines
Agrawal, AK
Jenekhe, SA
[J]. CHEMISTRY OF MATERIALS, 1996, 8 (02) : 579 - 589
[2] A new green approach to the Friedlander synthesis of quinolines
Arcadi, A
Chiarini, M
Di Giuseppe, S
Marinelli, F
[J]. SYNLETT, 2003, (02) : 203 - 206
[3] Identification of xanthurenic acid as the putative inducer of malaria development in the mosquito
Billker, O
Lindo, V
Panico, M
Etienne, AE
Paxton, T
Dell, A
Rogers, M
Sinden, RE
Morris, HR
[J]. NATURE, 1998, 392 (6673) : 289 - 292
[4] New protocol for Biginelli reaction-a practical synthesis of Monastrol
Bose, DS
Sudharshan, M
Chavhan, SW
[J]. ARKIVOC, 2005, : 228 - 236
[5] Green chemistry approaches to the synthesis of 5-alkoxycarbonyl-4-aryl-3,4-dihydropyrimidin-2(1H)-ones by a three-component coupling of one-pot condensation reaction:: Comparison of ethanol, water, and solvent-free conditions
Bose, DS
Fatima, L
Mereyala, HB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (02) : 587 - 590
[6] Bose DS, 2002, TETRAHEDRON LETT, V43, P9195
[7] Synthesis and antibacterial evaluation of certain quinolone derivatives
Chen, YL
Fang, KC
Sheu, JY
Hsu, SL
Tzeng, CC
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (14) : 2374 - 2377
[8] CHENG CC, 1982, ORG REACTIONS, V28, P37
[9] Synthesis of quinolines via ruthenium-catalysed amine exchange reaction between anilines and trialkylamines
Cho, CS
Oh, BH
Kim, JS
Kim, TJ
Shim, SC
[J]. CHEMICAL COMMUNICATIONS, 2000, (19) : 1885 - 1886
[10] Quinolines as potent 5-lipoxygenase inhibitors:: Synthesis and biological profile of L-746,530
Dubé, D
Blouin, M
Brideau, C
Chan, CC
Desmarais, S
Ethier, D
Falgueyret, JP
Friesen, RW
Girard, M
Girard, Y
Guay, J
Riendeau, D
Tagari, P
Young, RN
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (10) : 1255 - 1260

← 1 2 3 4 →