Abstract
4-Acetylantipyrine1 underwent condensation with 4-formyl-antipyrine2 to give3. Condensation of either3 with1 or1 with2 in a molar ratio of (2∶1) afforded4. Cyclization of4 in the presence of PPA and ammonium acetate or 4-aminoantipyrine in the presence of glacial acetic acid gave5–7, respectively. Claisen condensation of1 with ethyl acetate and diethyl oxalate afforded compounds8–10. The reaction of1 and2 with indole in ethanol/conc. hydrochloric acid was also investigated.
Similar content being viewed by others
Literature Cited
Wilson, C. O., Gisvold, O. and Doerge, R. F.: Textbook ofOrganic medicinal and pharmaceutical chemistry, 6th ed., p. 746, 1971, Lippincott Co., Philadelphia, Toronto.
Erlenmeyer, H. and Willi, E.: Relation between constitution and physiological activity of pyrazolone derivatives.Helv. Chem. Acta. 18, 740 (1935).
Prishchep, T. P.: Comparative pharmacological properties of some acylated 4-aminoantipyrine and of 1-phenyl-3-methyl-4-amino-5-pyrazolone. Farmakol. I Toksikol. 25, 55 (1962); C. A. 57, 13859 (1962).
Mario R. and Silvio Checchi (Univ. Florence): New derivatives of antipyrine, isoantipyrine and pyrazolidine.Ann. Chim. (Rome)43, 816 (1953). C. A.49, 6235 (1955).
Acheson, R. M.:An introduction to the chemistry of heterocyclic compounds, 2nd, ed., p. 239, 1967, John Wiley and Sons, Inc., New York, London, Sydney and Toronto.
Kataritzky, A. R.:Handbook of heterocyclic chemistry, 1st ed. pp. 404, 1985, Pergamon Press, Oxford, New York, Toronto, Sydney and Frankfurt.
Finar, I. L.: Preparation and properties of some bipyrazolyls.J. Chem. Soc., 1208 (1955).
Hamama, W. S., Hammouda, M. and Afsah, E. M.: Synthesis of 2-acetoacetyl-and 2-oxaloacetyl-1,3-indandiones and related compounds. Z. Naturforsch, 43b, 897 (1988).
Thesing, J.: Chemistry of indole III. The effect of alkali on quaternary salts of gramine.Chem. Ber.,87, 692 (1954).
Gray, A. P. and Archer, W. L.: Pyridylethylation of indole and related reactions.J. Am. Chem. Soc. 79, 3554 (1957).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Hammouda, M. Synthesis of some new 4-substituted antipyrines as potential antipyretic analgesics. Arch. Pharm. Res. 15, 1–4 (1992). https://doi.org/10.1007/BF02973975
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02973975