4,5-Dihydroisoxazole

Description

4,5-Dihydroisoxazoles (2-isoxazolines) contain an O-alkyl oxime moiety within a five-membered ring. These heterocycles draw tremendous interest as structural motifs of biologically active compounds and have established their position as synthons in synthetic organic chemistry. The compounds belonging to this class demonstrated their capacity to mask other functional groups for further functionalization of the ring to generate a variety of organic molecules.

Chemical Reactivity

4,5-Dihydroisoxazoles having a proton at the C3-position easily undergo isomerization under the influence of a base to generate β-hydroxynitriles. These heterocycles can also be converted to the corresponding amino alcohols through reduction of internal oxime functionality. Apart from these reactions, the selective scission of the N-O bond under various conditions has also been reported.