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Note | Regular issue | Vol 60, No. 10, 2003, pp. 2323 - 2342
Published online: 1st September, 2003
DOI: 10.3987/COM-03-9857
New 1-Substituted 4-Cinnamoyl-5-hydroxypyrazoles and Precursors Thereof: Synthesis, Ring Closure Reactions and NMR-Spectroscopic Investigations

Wolfgang Holzer* and Ingrid Krca

*Department of Pharmaceutical Chemistry, University of Vienna, Pharmaziezentrum, Althanstrasse14, A-1090 Vienna, Austria

Abstract

Reaction of 1-substituted 5-hydroxy-1H-pyrazoles (pyrazolones) with trans-cinnamoyl chloride / calcium hydroxide in dioxane affords the corresponding 4-cinnamoyl-5-hydroxy-1H-pyrazoles. Cyclization of the latter into 5,6-dihydropyrano[2,3-c]pyrazol-4-ones proceeds in very low yields upon treatment with concentrated sulfuric acid. 1,6-Diphenyl-1H-pyrano[2,3-c]pyrazol-4-one was synthesized by reaction of of 4-acetyl-5-hydroxy-1-phenyl-1H-pyrazole with benzoyl chloride and lithium bis(trimethylsilyl)amide and subsequent cyclization of the thus obtained 1,3-diketone. NMR-spectroscopic investigations with the obtained 4-substituted 5-hydroxypyrazoles and their precursors regarding their tautomeric behavior in various solvents are presented.

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