1,2-Benzisoxazole is anaromaticorganic compound with a molecular formula C7H5NO containing abenzene-fusedisoxazole ring structure.[1][2] The compound itself has no common applications; however, functionalizedbenzisoxazoles andbenzisoxazoyls have a variety of uses, including pharmaceutical drugs such as some antipsychotics (includingrisperidone,paliperidone,ocaperidone, andiloperidone) and the anticonvulsantzonisamide.
Itsaromaticity makes it relatively stable;[3] however, it is only weakly basic.
^Katritzky, A. R.; Pozharskii, A. F. (2000).Handbook of Heterocyclic Chemistry (2nd ed.). Academic Press.ISBN0080429882.
^Clayden, J.; Greeves, N.; Warren, S.; Wothers, P. (2001).Organic Chemistry. Oxford, Oxfordshire: Oxford University Press.ISBN0-19-850346-6.
^Domene, Carmen; Jenneskens, Leonardus W.; Fowler, Patrick W. (2005). "Aromaticity of anthranil and its isomers, 1,2-benzisoxazole and benzoxazole".Tetrahedron Letters.46 (23):4077–4080.doi:10.1016/j.tetlet.2005.04.014.hdl:1874/14837.ISSN0040-4039.
^Casey, Martha L.; Kemp, D. S.; Paul, Kenneth G.; Cox, Daniel D. (June 1973). "Physical organic chemistry of benzisoxazoles. I. Mechanism of the base-catalyzed decomposition of benzisoxazoles".The Journal of Organic Chemistry.38 (13):2294–2301.doi:10.1021/jo00953a006.
^Kemp, D. S.; Cox, Daniel D.; Paul, Kenneth G. (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.97 (25):7312–7318.doi:10.1021/ja00858a018.
^Kemp, Daniel S. (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.92 (8):2553–2554.doi:10.1021/ja00711a061.
