A rapid and general access to 3-arylpiperidines

被引:11
作者
Büchner, IK [1 ]
Metz, P [1 ]
机构
[1] Tech Univ Dresden, Inst Organ Chem, D-01062 Dresden, Germany
关键词
physiologically active compounds; piperidines; Heck reactions; ozonolysis;
D O I
10.1016/S0040-4039(01)01045-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A short and efficient synthetic sequence to produce a wide variety of 3-arylpiperidines from three simple building blocks is described. The key step is a palladium-catalyzed arylation of cyclopentene. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5381 / 5383
页数:3
相关论文
共 20 条
[1]   Asymmetric routes to substituted piperidines [J].
Bailey, PD ;
Millwood, PA ;
Smith, PD .
CHEMICAL COMMUNICATIONS, 1998, (06) :633-640
[2]   The heck reaction as a sharpening stone of palladium catalysis [J].
Beletskaya, IP ;
Cheprakov, AV .
CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066
[3]   Conformational effects on the activity of drugs part 21 -: N-n-propyl-substitute 3-(dimethylphenyl)piperidines display novel discriminative properties between dopamine receptor subtypes:: Synthesis and receptor binding studies [J].
Cervetto, L ;
Demontis, GC ;
Giannaccini, G ;
Longoni, B ;
Macchia, B ;
Macchia, M ;
Martinelli, A ;
Orlandini, E .
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (25) :4933-4938
[4]   DOPAMINE RECEPTOR AGONISTS - MECHANISMS UNDERLYING AUTORECEPTOR SELECTIVITY .2. THEORETICAL CONSIDERATIONS [J].
CLARK, D ;
HJORTH, S ;
CARLSSON, A .
JOURNAL OF NEURAL TRANSMISSION, 1985, 62 (3-4) :171-207
[5]   DOPAMINE-RECEPTOR AGONISTS - MECHANISMS UNDERLYING AUTORECEPTOR SELECTIVITY .1. REVIEW OF THE EVIDENCE [J].
CLARK, D ;
HJORTH, S ;
CARLSSON, A .
JOURNAL OF NEURAL TRANSMISSION, 1985, 62 (1-2) :1-52
[6]   Palladium in action:: domino coupling and allylic substitution reactions for the efficient construction of complex organic molecules [J].
de Meijere, A ;
Bräse, S .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) :88-110
[7]  
GRAYSON NA, 1992, HETEROCYCLES, V34, P2281
[8]   Antipsychotic properties of the partial dopamine agonist (-)-3-(3-hydroxyphenyl)-N-n-propylpiperidine (preclamol) in schizophrenia [J].
Lahti, AC ;
Weiler, MA ;
Corey, PK ;
Lahti, RA ;
Carlsson, A ;
Tamminga, CA .
BIOLOGICAL PSYCHIATRY, 1998, 43 (01) :2-11
[9]   IMPROVED PROCEDURES FOR THE PALLADIUM-CATALYZED INTERMOLECULAR ARYLATION OF CYCLIC ALKENES [J].
LAROCK, RC ;
GONG, WH ;
BAKER, BE .
TETRAHEDRON LETTERS, 1989, 30 (20) :2603-2606
[10]   PALLADIUM-CATALYZED INTERMOLECULAR ALLYLIC ARYLATION OF CYCLOALKENES [J].
LAROCK, RC ;
BAKER, BE .
TETRAHEDRON LETTERS, 1988, 29 (08) :905-908