2-Isoxazolines have been known for some time as potential pharmacophores, bioisosteres, and protective groups for β-hydroxyketones. Their preparation via the typical 1,3-dipolar cycloaddition presents numerous issues associated with regio- and stereo-selection. We have evaluate the ring closing of a β,γ-unsaturated oxime, a process that reduces these issues but yet still provides the desired isoxazoline in good yield. Herein, we report the application of this methodology to the use of α,β-unsaturated oximes resulting from the oximation of substituted chalcones. Initially, the chalcone is prepared by aldol condensation of appropriately substituted benzaldehydes and acetophenones. The results of this exploration and issues centered on the methodology will be discussed.

Cyclization of α,β-unsaturated oximes

254th National Meeting (2017)

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