Stereoselective transformation of pyrazinones into substituted analogues of cis-5-amino-6-oxo-2-piperidinemethanol and cis-5-amino-2-piperidinemethanol

被引：15
|
作者：
Rogiers, J [1 ]
De Borggraeve, WM [1 ]
Toppet, SM [1 ]
Compernolle, F [1 ]
Hoornaert, GJ [1 ]
机构：
[1] Katholieke Univ Leuven, Dept Organ Chem, Organ Synth Lab, B-3001 Louvain, Belgium
来源：
TETRAHEDRON | 2003年 / 59卷 / 27期
关键词：
substituted piperidines; substituted piperidinones; Diels-Alder reaction; Substance P antagonists;
D O I：
10.1016/S0040-4020(03)00741-5
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Various analogues of cis-5-amino-6-oxo-2-piperidinemethanol and c-is-5-amino-2-piperidinemethanol have been prepared via Diels-Alder reaction of substituted pyrazinones with ethene followed by acid methanolysis of the bridged lactam adducts. Further reduction of the resulting methyl 2-piperidinecarboxylate ester compounds led to the corresponding 2-piperidinemethanol products that were converted into potential SP antagonists. (C) 2003 Elsevier Science Ltd. All rights reserved.
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页码：5047 / 5054
页数：8
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