Английская Википедия:Benzisoxazole

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1,2-Benzisoxazole is an aromatic organic compound with a molecular formula C7H5NO containing a benzene-fused isoxazole ring structure.[1][2] 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;[3] 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.[4]

Synthesis of 1,2-Benzisoxazol aus Salicylaldehyd und HOSA
Synthesis of 1,2-Benzisoxazol aus Salicylaldehyd und HOSA

Reactions

Kemp elimination

First reported by Daniel S. Kemp,[5][6][7] the relatively weak N-O bond can be cleaved by a strong base to yield a 2-hydroxybenzonitrile species.

Файл:Kemp-Eliminierung Reaktionsmechanismus V3.svg

See also

Structural isomers

References

Шаблон:Reflist

Шаблон:Simple aromatic rings