Benzisoxazole

 ( Aromatic Bases ) 

1,2-Benzisoxazole is an aromatic organic compound with a molecular formula C₇H₅NO containing a benzene-fused isoxazole ring structure.

The compound itself has no common applications; however, functionalized benzisoxazoles and benzisoxazoyls have a variety of uses, including pharmaceutical drugs such as some antipsychotics (including risperidone, paliperidone, ocaperidone, and iloperidone) and the anticonvulsant zonisamide.

Its aromaticity makes it relatively stable; however, it is only weakly basic.

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Synthesis Benzisoxazole may be prepared from inexpensive salicylaldehyde, via a base catalyzed room temperature reaction with hydroxylamine- O-sulfonic acid.

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Reactions

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Kemp elimination First reported by Daniel S. Kemp, the relatively weak N-O bond can be cleaved by a strong base to yield a 2-hydroxybenzonitrile species.

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See also

Structural isomers

• Benzoxazole
• Anthranil

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