Abstract
3 : 5-Dimethyl-4-nitro isoxazole and 3-aryl-2-isoxazolin-5-ones were found to undergo the Mannich reaction readily at room temperature, affording in most cases unstable products. While the 5-methyl group was the active site with the former, the latter underwent reaction exclusively at the 4-position. The structures of the products were confirmed by spectral data. The Mannich bases from the isoxazolones were found to exist in three tautomeric modifications, contrary to earlier observations. Most of the products exhibited a high degree of antibacterial activity.
Similar content being viewed by others
References
French Patent 20,81,594 (1972);C.A. 77 114382 (1972).
Sciortino, T. and du Ban, G.,Boll. Chim. Farm. 105 807 (1966).
French Patent 14,77,409 (1967);C.A. 67 108560 (1967).
Verma, R. S. and Nobles, W. L.,J. Med. Chem. 11 195 (1967).
Kano, H.et al., J. Med. Chem. 10 1587 (1966).
Kano, H.et al, Japanese Patent 7006 (1970);C.A. 68 59566 (1968).
Kano, H.et al, Japanese Patent 9830 (1967);C.A. 72 121509 (1970).
Zinner, G., Boehlke, B., Weber, K. O., Moll, R. and Denker, W.,Arch. Pharm. 299 222, (1966).
Barbieri, W.et al, Tetrahedron 23 4409 (1967).
Summers, L. A., Byrde, R. J. W. and Hislop, E. C.,Ann. Appl. Biol. 62 45 (1968).
Quilico, A., in Arnold Weissberger’sChemistry of Heterocyclic Compounds, Vol. 17. Wiley-Interscience p. 105 (1962).
Kochetkov, N. K. and Sokolov, S. inAdvances in Heterocyclic Chemistry, Vol. 2, ed. Katritzky, A. R. Academic Press p. 299 (1963).
Morgan, G. T. and Burgess, H.,J. Chem. Soc. 119 697 (1921).
Katritzky, A. R., inPhysical Methods in Heterocyclic Chemistry, Vol. 2, Academic Press p. 233 (1972).
Morley, E. G.,J. Path. Bact. 57 379 (1945).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Rao, K.S.R.K.M., Devi, Y.U. A study of the Mannich reaction in the isoxazole series. Proc. Indian Acad. Sci. 84, 79–84 (1976). https://doi.org/10.1007/BF03046645
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF03046645