Abstract
As part of a research programme targeting novel molecules derived from nitrogen derivatives of o-hydroxyaryl ketones [1] we synthesised 7-hydroxy-8-acetylcoumarin oxime and we subsequently oxidized it with lead tetraacetate (LTA) as well as with diacetoxy iodobenzene (DIB).[...]
Highlights
As part of a research programme targeting novel molecules derived from nitrogen derivatives of ohydroxyaryl ketones [1] we synthesised 7-hydroxy-8-acetylcoumarin oxime and we subsequently oxidized it with lead tetraacetate (LTA) as well as with diacetoxy iodobenzene (DIB)
7-Hydroxy-8-acetylcoumarin oxime was prepared according to the literature method [4] whereas commercially available lead tetraacetate as well as diacetoxy iodobenzene were supplied by Aldrich
Filtration of the precipitate, which was formed, gave a solid which was recrystillised from petroleum ether to afford (0.33 g, 67 %) of the desired as white crystals
Summary
Received: 24 April 2007; in revised form: 8 August 2008 / Accepted: 18 August 2008 / Published: 24 August 2008. As part of a research programme targeting novel molecules derived from nitrogen derivatives of ohydroxyaryl ketones [1] we synthesised 7-hydroxy-8-acetylcoumarin oxime and we subsequently oxidized it with lead tetraacetate (LTA) as well as with diacetoxy iodobenzene (DIB). The reactions led to the formation of the oxidative cyclisation product, 9-methyl-2H-chromeno[8,7-d]isoxazol-2-one N-oxide , in good yields. It is well known that isoxazole ring possesses interesting biological activity especially as acetyl cholesterinase inhibitor [2] and as antimicrobial agent [3]
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