Synthesis of 3-arylisoxazoles and 5-arylisoxazoles

No Thumbnail Available
Pertler, Stephanie L.
Sammelson, Robert E.
Issue Date
Thesis (M.S.)
Department of Chemistry
Other Identifiers

The goal of this research project was to synthesize a small library of 3- and 5-arylisoxazoles. These compounds are of interest because of potential biological activity similar to Fipronil. Fipronil is used commercially in the agrochemical industry and exhibits pesticidal activity as a noncompetitive inhibitor of the GABA receptor. By deleting the amino group normally at the 5-position and the cyano group normally at the 3-position and changing the atoms in the heterocyclic ring from containing two nitrogen atoms to one nitrogen and one oxygen atom, we hope to create changes in the binding so the geometry of the GABA receptor may be better understood.The synthesis of our target compounds consisted of many steps. First, brominated intermediates were made from commercially available compounds. The brominated intermediates were converted to aldehydes, which then produced oximes. The oximes were then combined with alkynes through a 1,3-dipolar cycloaddition to form the arylisoxazoles.