Syntheses of acetylquinolines and acetylisoquinolines via palladium-catalyzed coupling reactions

被引：56

作者：

Legros, JY ^{[1
]}

Primault, G ^{[1
]}

Fiaud, JC ^{[1
]}

机构：

[1] Univ Paris Sud, Inst Chim Mol Orsay, UPRESA 8075, Lab Catalyse Mol,CNRS, F-91405 Orsay, France

来源：

TETRAHEDRON | 2001年 / 57卷 / 13期

关键词：

isoquinolines; quinolines; Heck reaction; Stille reaction;

D O I：

10.1016/S0040-4020(01)00076-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Acetylquinolines and acetylisoquinolines were obtained from the corresponding chloro-, bromo- or trifluoromethylsulfonyloxy-heteroaromatics via four different palladium-catalyzed coupling reactions: (i) Stille coupling with tri(n-butyl)-1-ethoxyvinylstannane; (ii) Negishi coupling with 1-ethoxyvinylzinc chloride; (iii) cross-coupling with tri(1-ethoxyvinyl)indium; (iv) Heck arylation of n-butyl vinyl ether. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：2507 / 2514

页数：8

共 37 条

[1] PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ARYLBORONIC ACIDS WITH PI-DEFICIENT HETEROARYL CHLORIDES
ALI, NM
MCKILLOP, A
MITCHELL, MB
REBELO, RA
WALLBANK, PJ
[J]. TETRAHEDRON, 1992, 48 (37) : 8117 - 8126
[2] Arylmethyl esters as protecting groups for carboxylic, carbonic and carbamic acids: deprotection via homogeneous palladium-catalyzed hydrogenolysis
Boutros, A
Legros, JY
Fiaud, JC
[J]. TETRAHEDRON LETTERS, 1999, 40 (41) : 7329 - 7332
[3] 4-Quinolylmethyl and 1-naphthylmethyl as benzyl-type protecting groups of carboxylic acids removable by homogeneous palladium-catalyzed hydrogenolysis
Boutros, A
Legros, JY
Fiaud, JC
[J]. TETRAHEDRON, 2000, 56 (15) : 2239 - 2246
[4] ALPHA-REGIOSELECTIVITY IN PALLADIUM-CATALYZED ARYLATION OF ACYCLIC ENOL ETHERS
CABRI, W
CANDIANI, I
BEDESCHI, A
PENCO, S
SANTI, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (05) : 1481 - 1486
[5] PALLADIUM-CATALYZED ARYLATION OF UNSYMMETRICAL OLEFINS - BIDENTATE PHOSPHINE LIGAND CONTROLLED REGIOSELECTIVITY
CABRI, W
CANDIANI, I
BEDESCHI, A
SANTI, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (13) : 3558 - 3563
[6] PALLADIUM-MEDIATED TRANSFORMATIONS OF HETEROAROMATIC TRIFLATES
CRISP, GT
PAPADOPOULOS, S
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1989, 42 (02) : 279 - 285
[7] ANALOGUES OF 2,2'-BIPYRIDYL WITH ISOQUINOLINE AND THIAZOLE RINGS .2.
CROWNE, FR
BRECKENRIDGE, JG
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1954, 32 (07): : 641 - 645
[8] 1,2-ADDITIONS TO HETEROATOM-SUBSTITUTED OLEFINS BY ORGANOPALLADIUM REAGENTS
DAVES, GD
HALLBERG, A
[J]. CHEMICAL REVIEWS, 1989, 89 (07) : 1433 - 1445
[9] 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
[10] PALLADIUM-CATALYZED COUPLING OF ARYL TRIFLATES WITH ORGANOSTANNANES
ECHAVARREN, AM
STILLE, JK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) : 5478 - 5486

← 1 2 3 4 →