A Regioselective Route to 5-Substituted Isoxazole- and Isoxazoline-3-phosphonates

被引：9

作者：

Conti, Paola ^{[1
]}

Pinto, Andrea ^{[1
]}

Tamborini, Lucia ^{[1
]}

Dunkel, Petra ^{[1
]}

Gambaro, Veniero ^{[1
]}

Visconti, Giacomo L. ^{[1
]}

De Micheli, Carlo ^{[1
]}

机构：

[1] Univ Milan, Dipartimento Sci Farmaceut P Pratesi, I-20133 Milan, Italy

来源：

SYNTHESIS-STUTTGART | 2009年 / 04期

关键词：

cycloadditions; regioselectivity; phosphonates; isoxazoles; heterocycles; GLUTAMATE RECEPTORS; PHARMACOLOGICAL CHARACTERIZATION; PHOSPHORYLNITRILE OXIDE; CYCLOADDITION; HOMOLOGS; ACID; ENANTIOPHARMACOLOGY; SPIROISOXAZOLINE; ASSIGNMENT; CALAFIANIN;

D O I：

10.1055/s-0028-1083343

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

5-Substituted 3-(diethoxyphosphoryl)isoxazoles and -2-isoxazolines were synthesized regioselectively by 1,3-dipolar cycloaddition of(diethoxyphosphoryl)formonitrile oxide to monosubstituted alkynes and alkenes. By applying this methodology to an N-(tert-butoxycarbonyl)-substituted allylglycine methyl ester, we prepared the precursors of two diastereomeric 3-phosphono-2-isoxazolin-5-yl-substituted amino acids, which are bioisosteres of potent NMDA receptor antagonists.

引用

页码：591 / 596

页数：6

共 32 条

[1] Gastrointestinal effects of selective and non-selective non-steroidal anti-inflammatory drugs [J].