Reaction of (Z)-4-((dimethylamino)methylene)-1-phenylpyrazolidine-3,5-dione (1) with different nucleophiles is described. Treatment of enaminone 1 with phenylhydrazine led to 3-oxo-N’,2-diphenyl-2,3-dihydro-1H-pyrazole-4-carbohydrazide 7. New enaminone derivatives 2–6 and 12–14 were conveniently obtained in high yields via nucleophilic substitution of the dimethylamino group in enaminone 1 when reacted with o-aminophenol, o-aminothiophenol, ethanolamine, cysteamine hydrochloride, piperidine, morpholine, 2-aminopyridine and glycine. Reaction of enaminone 1 with diaza-nucleophiles, such as hydrazine hydrate, ethylenediamine and o-phenylenediamine, afforded the corresponding bis-enaminones 9–11. Anti-inflammatory and antimicrobial activities of some new products were evaluated. Compounds 1, 2, 4, 7, 12a, and 12b showed high anti-inflammatory activity compared with indomethacin as the reference, while the highest antimicrobial effect was observed in the case of compound 3.
CITATION STYLE
Ahmed, E. A. (2015). Convenient synthesis and biological activity of 4-Aminomethylene 1-Phenylpyrazolidine-3,5-diones. Journal of the Mexican Chemical Society, 59(3), 181–190. https://doi.org/10.29356/jmcs.v59i3.33
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