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The Preparation of 2-Isoxazolines from O-Propargylic Hydroxylamines via a Tandem Rearrangement-Cyclisation Reaction

Lewis Pennicott, Stephen Lindell*

*Bayer CropScience GmbH, Werk Höchst G836, 65926 Frankfurt am Main, Germany, Email:

L. Pennicott, S. Lindell, Synlett, 2006, 463-465.

DOI: 10.1055/s-2006-926232

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3-alkylpropargyl or 3-arylpropargyl hydroxylamines hydrochlorides were converted to 2-isoxazolines in good yields in refluxing methanol in the presence of K2CO3. Methods for 3-unsubstituted compounds and the direct transformation of a O-propargyl phthalimide into 2-isoxazolines were also developed.

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Key Words

isoxazoline synthesis, O-propargylic hydroxylamine, sigmatropic rearrangement

ID: J60-Y2006-4280