Benzisoxazole

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 and the anticonvulsant zonisamide.
Its aromaticity makes it relatively stable; however, it is only weakly basic.

Synthesis

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

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.