5-Substituted 3-(diethoxyphosphoryl)isoxazoles and -2- isoxazolines were synthesized regioselectively by 1,3-dipolar cy- cloaddition of (diethoxyphosphoryl)formonitrile oxide to monosub- stituted 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-isoxazo- lin-5-yl-substituted amino acids, which are bioisosteres of potent NMDA receptor antagonists.
A regioselective route to 5-substituted isoxazoline-3-phosphonates / P. Conti, A. Pinto, L. Tamborini, P. Dunkel, V. Gambaro, G.L. Visconti, C. De Micheli. - In: SYNTHESIS. - ISSN 0039-7881. - 2009:4(2009), pp. 591-596.
Titolo: | A regioselective route to 5-substituted isoxazoline-3-phosphonates |
Autori: | CONTI, PAOLA (Primo) PINTO, ANDREA (Secondo) VISCONTI, GIACOMO LUCA (Penultimo) DE MICHELI, CARLO (Ultimo) |
Settore Scientifico Disciplinare: | Settore CHIM/08 - Chimica Farmaceutica |
Data di pubblicazione: | 2009 |
Rivista: | |
Tipologia: | Article (author) |
Digital Object Identifier (DOI): | http://dx.doi.org/10.1055/s-0028-1083343 |
Appare nelle tipologie: | 01 - Articolo su periodico |