Benzo[b]thiophene as a template for substituted quinolines and tetrahydroquinolines

被引:26
作者
Chabert, JFD
Chatelain, G
Pellet-Rostaing, S
Bouchu, D
Lemaire, M
机构
[1] CPE Lyon, UMR 5181, Lab Catalyse & Synth Organ, F-69616 Villeurbanne, France
[2] Ctr Spect Masse, UMR 5181, F-69616 Villeurbanne, France
关键词
Nickel hydrogenation; diarylquinolines; diaryltetrahydroquinolines;
D O I
10.1016/j.tetlet.2005.11.108
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An original methodology starting from 3-aroyl-2-(2'-nitro-4'-methoxyphenyl)-benzo[b]thiophene allows the synthesis of unusual fused heterocycles. Direct hydrogenation with nickel catalysts followed by desulfurisation led to 2,3-diarylquinolines or 2,3-diaryltetrahydroquinolines. (c) 2005 Published by Elsevier Ltd.
引用
收藏
页码:1015 / 1018
页数:4
相关论文
共 36 条
[1]   A valuable heterocyclic ring transformation:: from isoxazolin-5(2H)-ones to quinolines [J].
Abbiati, G ;
Beccalli, EM ;
Broggini, G ;
Zoni, C .
TETRAHEDRON, 2003, 59 (50) :9887-9893
[2]   The assembly of oligonuclear nickel(II) complexes from asymmetric compartmental ligands in the presence of alkali metal salts [J].
Adams, H ;
Fenton, DE ;
McHugh, PE .
INORGANIC CHEMISTRY COMMUNICATIONS, 2004, 7 (02) :147-150
[3]   A new green approach to the Friedlander synthesis of quinolines [J].
Arcadi, A ;
Chiarini, M ;
Di Giuseppe, S ;
Marinelli, F .
SYNLETT, 2003, (02) :203-206
[4]   DESULFURIZATION OF BENZOTHIOPHENES AND DIBENZOTHIOPHENES WITH NICKEL BORIDE [J].
BACK, TG ;
YANG, KX ;
KROUSE, HR .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) :1986-1990
[5]   DESULFURIZATION WITH NICKEL AND COBALT BORIDE - SCOPE, SELECTIVITY, STEREOCHEMISTRY, AND DEUTERIUM-LABELING STUDIES [J].
BACK, TG ;
BARON, DL ;
YANG, KX .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (09) :2407-2413
[6]   NEW DESULFURIZATIONS BY NICKEL-CONTAINING COMPLEX REDUCING AGENTS [J].
BECKER, S ;
FORT, Y ;
CAUBERE, P .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (25) :6194-6198
[7]   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
[8]   The [(E,E,E)-1,6,11-tris(p-toluenesulfonyl)-1,6,11-triazacyclopentadeca-3,18,13-triene]Pd(0) complex in the hydroarylation of alkynes in ionic liquids.: An approach to quinolines [J].
Cacchi, S ;
Fabrizi, G ;
Goggiamani, A ;
Moreno-Mañas, M ;
Vallribera, A .
TETRAHEDRON LETTERS, 2002, 43 (32) :5537-5540
[9]   ANTICONVULSANT ACTIVITY OF GLYCINE-SITE NMDA ANTAGONISTS .2. TRANS 2-CARBOXY-4-SUBSTITUTED TETRAHYDROQUINOLINES [J].
CARLING, RW ;
LEESON, PD ;
MOSELEY, AM ;
SMITH, JD ;
SAYWELL, K ;
TRICKLEBANK, MD ;
KEMP, JA ;
MARSHALL, GR ;
FOSTER, AC ;
GRIMWOOD, S .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (01) :65-70
[10]   An efficient phosphine-free palladium coupling for the synthesis of new 2-arylbenzo[b]thiophenes [J].
Chabert, JFD ;
Joucla, L ;
David, E ;
Lemaire, M .
TETRAHEDRON, 2004, 60 (14) :3221-3230