Reaction of β-nitroenones with thiophenol synthesis of 5-hydroxy-4-(phenylthio)-2-isoxazoline 2-oxides

Add time:08/03/2019    Source:sciencedirect.com

A new synthesis of 2-isoxazoline 2-oxides starting from unsaturated nitro compounds is described. A facile and convenient preparation of β-alkyl substituted β-nitroenones and their conversion to β-nitrosulfides are recorded. Treatment of these compounds with potassium tert-butoxide at −78°C followed by immediate quenching with acetic acid provides access to 5-hydroxy-4-(phenylthio)-2-isoxazoline 2-oxides via intramolecular addition of the nitronate anion to the carbonyl group.

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