Beilstein J. Org. Chem.2007,3, No. 20, doi:10.1186/1860-5397-3-20
)-one-2,2-dioxide Y = H), an obvious precursor for 5, was reported by Timoney et al., in an overall yield of ~30% [1] via the cyclisation of the methanesulfonate of salicylaldehyde followed by oxidation (Scheme 4).
Results and discussion
In order to prepare 6 in better yield, we choose methyl salicylate
methanesulfonate of salicylaldehyde.
Preparation of 1,2-benzoxathiin-4(3H)-one-2,2-dioxides.
Preparation of sultone oximes.
Preparation of 3-alkyl-1,2-benzisoxazole derivatives.
Synthesis of zonisamide from 1,2-benzisoxazole-3-methane-sulfonate.
Compounds 6a-i prepared.
Compounds 5a-i prepared.
Compounds 10a-i
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Graphical Abstract
Scheme 1:
Conversion of coumarin-4-one oximes to 3-alkyl-1,2-benzisoxazole derivatives.