Synthesis and structural study of 3,4-dihydro-2(1H)-pyridones and isoxazolo[5,4-b]pyridin-6(7H)-ones

被引：0
|
作者：
Suárez, M
Verdecia, Y
Ochoa, E
Salfrán, E
Morán, L
Martín, N
Martínez, R
Quinteiro, M
Seoane, C
Soto, JL
Novoa, H
Blaton, N
Peeters, OM
De Ranter, C
机构：
[1] Univ La Habana, Fac Quim, Lab Sintesis Organ, Havana 10400, Cuba
[2] Univ Complutense Madrid, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain
[3] Ctr Quim Farmaceut, Havana, Cuba
[4] Catholic Univ Louvain, Fac Farmaceut Wetenschappen, Lab Analyt Chem Med Fysicochem, B-3000 Louvain, Belgium
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 2000卷 / 11期
关键词：
isoxazolo[5,4-b]pyridin-6(7H)-ones; 3,4-dihydro-2(1H)pyridones; calcium channel modulators; conformation analysis; asymmetric synthesis; semiempirical calculations;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of isoxazolo[5,4-b]pyridin-6(7H)-ones (8) have been prepared with a high stereochemical control from the novel 3,4-dihydro-2(1H)-pyridones (7) by reaction with hydroxylamine hydrochloride and subsequent 5-endo-trig cyclization. A structural study by X-ray analyses and theoretical calculations (AM1) of both heterocyclic systems (7 and 8) shows a favoured conformer with the aryl group on C4 in a pseudoaxial position. The same favoured conformation was found in solution according to NOE experiments and comparison of theoretical and experimental. coupling constants.
引用
收藏
页码：2079 / 2088
页数：10
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