Novel base catalysed rearrangement of sultone oximes to 1,2-benzisoxazole- 3-methane sulfonate derivatives

• Veera Reddy Arava,
• Udaya Bhaskara Rao Siripalli,
• Vaishali Nadkarni and
• Rajendiran Chinnapillai

Beilstein J. Org. Chem. 2007, 3, No. 20, doi:10.1186/1860-5397-3-20

• -3-methanesulfonates and 4-oximino-2,3-dihydrobenzoxathiin-2,2-dioxides (sultone oximes) is described. These compounds are important intermediates for the preparation of zonisamide, an anti-convulsant drug. Background 3-Alkyl-1,2-benzisoxazole derivatives are known to have important biological

• was developed by Dianippon of Japan. Compounds 1 were originally prepared from the rearrangement of coumarin-4-one oximes 3 as shown in Scheme 1. The 1,2-benzisoxazole-3-acetic acids were converted into halogenated compounds, then reacted with various different nucleophiles to generate the compounds 1

• ) failed to produce the cyclised products and gave only salicylic acid derivatives. All the 1,2-benzoxathiin-4(3H)-one-2,2-dioxides 6 were characterised from their analytical and spectral data. Conversion of ketones 6 into the corresponding oximes 5 proceeded uneventfully, and oximes 5 were characterised