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

页码：2079 / 2088

页数：10

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