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: Stephen.lindellbayercropscience.com
L. Pennicott, S. Lindell, Synlett, 2006, 463-465.
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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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isoxazoline synthesis, O-propargylic hydroxylamine, sigmatropic rearrangement