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Benzisoxazole

Benzisoxazole

101-102 °C (at 2 kPa)

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.

Synthesis

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

:[[File:1,2-Benzisoxazol.svg|300px|center|Synthesis of 1,2-Benzisoxazol aus Salicylaldehyd und HOSA]]

Reactions

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.

References

References

  1. {{Katritzky2nd
  2. Clayden, J.. (2001). "Organic Chemistry". Oxford University Press.
  3. (2005). "Aromaticity of anthranil and its isomers, 1,2-benzisoxazole and benzoxazole". Tetrahedron Letters.
  4. (1965). "The N-ethylbenzisoxazolium cation—I". Tetrahedron.
  5. (June 1973). "Physical organic chemistry of benzisoxazoles. I. Mechanism of the base-catalyzed decomposition of benzisoxazoles". The Journal of Organic Chemistry.
  6. (December 1975). "Physical organic chemistry of benzisoxazoles. IV. Origins and catalytic nature of the solvent rate acceleration for the decarboxylation of 3-carboxybenzisoxazoles". Journal of the American Chemical Society.
  7. (April 1970). "Decarboxylation of benzisoxazole-3-carboxylic acids. Catalysis by extraction of possible relevance to the problem of enzymic mechanism". Journal of the American Chemical Society.
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aromatic-bases benzisoxazoles simple-aromatic-rings
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