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

Arava VR, Siripalli UB, Nadkarni V, Chinnapillai R - Beilstein J Org Chem (2007)

Bottom Line: A new process for the preparation of 1,2-benzisoxazole-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.

View Article: PubMed Central - HTML - PubMed

Affiliation: Research and Development Laboratories, Suven Life Sciences Ltd,, # 18, Phase - III, Jeedimetla, Hyderabad - 500055, India. reddyvenis@rediffmail.com

ABSTRACT
A new process for the preparation of 1,2-benzisoxazole-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.

No MeSH data available.


Synthesis of 1,2-benzoxathiin-4(3H)-one-2,2-dioxide 6 from methanesulfonate of salicylaldehyde.
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C4: Synthesis of 1,2-benzoxathiin-4(3H)-one-2,2-dioxide 6 from methanesulfonate of salicylaldehyde.

Mentions: The synthesis of compounds 5 has not been reported in the literature. Synthesis of compound 6 (1,2-benzoxathiin-4(3H)-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).


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

Arava VR, Siripalli UB, Nadkarni V, Chinnapillai R - Beilstein J Org Chem (2007)

Synthesis of 1,2-benzoxathiin-4(3H)-one-2,2-dioxide 6 from methanesulfonate of salicylaldehyde.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC1919382&req=5

C4: Synthesis of 1,2-benzoxathiin-4(3H)-one-2,2-dioxide 6 from methanesulfonate of salicylaldehyde.
Mentions: The synthesis of compounds 5 has not been reported in the literature. Synthesis of compound 6 (1,2-benzoxathiin-4(3H)-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).

Bottom Line: A new process for the preparation of 1,2-benzisoxazole-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.

View Article: PubMed Central - HTML - PubMed

Affiliation: Research and Development Laboratories, Suven Life Sciences Ltd,, # 18, Phase - III, Jeedimetla, Hyderabad - 500055, India. reddyvenis@rediffmail.com

ABSTRACT
A new process for the preparation of 1,2-benzisoxazole-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.

No MeSH data available.