Add time:07/30/2019         Source:sciencedirect.com

The exocyclic double bond in 4-arylidene-3-substituted-isoxazolin-5-one (I) undergoes addition reactions with Grignard reagents and with benzene in the presence of aluminium chloride. Treatment of 4-arylazo derivatives of 3-substituted-isoxazolin-5-ones (III) with Grignard reagents does not effect hetero-ring opening and only the carbonyl group of III enters into reaction, followed by elimination of the elements of water on acidifcation, yielding 3-substituted-4-arylazo-5-arylisoxazoles (IV). Deacylation of 4-acetyl-3-phenylisoxazoline-5-one (VI) is achieved by the action of organomagnesium compounds, magnesium-magnesium iodide mixture, and/or lithium aluminium hydride.3,4-Disubstituted-5-methoxyisoxazoles (X) are readily obtained upon treatment of II with diazomethane. 2-Methyl-3,4-disubstituted-isoxazolin-5-one (XI) are produced via the action of methyl iodide on the silver salt of II and/or via the action of dimethyl sulphate on IIa directly.

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