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.