Synthesis 2011(8): 1255-1260  
DOI: 10.1055/s-0030-1258477
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Regioselective Preparation of Functionalized Isoxazoline Derivatives as Key Intermediates for the Synthesis of Selective N-Methyl-d-aspartate Receptor Antagonists

Lucia Tamborini*a, Andrea Pintoa, Paola Contia, Maddalena Gallantia, Maria Celeste Iannuzzia, Leonardo Lo Prestib, Carlo De Michelia
a Dipartimento di Scienze Farmaceutiche ‘Pietro Pratesi’, Università degli Studi di Milano, Via Mangiagalli 25, 20133 Milano, Italy
Fax: +39(02)50319326; e-Mail: lucia.tamborini@unimi.it;
b Dipartimento di Chimica Fisica ed Elettrochimica, Università degli Studi di Milano, Via Golgi 19, 20133 Milano, Italy
Further Information

Publication History

Received 10 December 2010
Publication Date:
16 March 2011 (online)

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Abstract

Two highly versatile isoxazoline derivatives, as key intermediates for the synthesis of differently functionalized subtype-selective N-methyl-d-aspartate receptor antagonists, were designed and synthesized. The synthetic strategy is based on an intramolecular nitrile oxide cycloaddition reaction which is a powerful method capable of controlling both the regio- and stereochemistry of the pericyclic reaction.