Formation of 5-Aminomethyl-2,3-dihydropyridine-4(1H)-ones from 4-Amino-tetrahydropyridinylidene Salts

Formation of 5-Aminomethyl-2,3-dihydropyridine-4(1H)-ones from 4-Amino-tetrahydropyridinylidene Salts

Various 4-aminotetrahydropyridinylidene salts were treated with aldehydes in an alkaline medium. Their conversion to 5-substituted β-hydroxyketones in a one-step reaction succeeded only with an aliphatic aldehyde. Instead, aromatic aldehydes gave 5-substituted β-aminoketones or a single δ-diketone....

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Veröffentlicht in:Molecules (Basel, Switzerland) Switzerland), 2023-09, Vol.28 (19), p.6869
Hauptverfasser: Seebacher, Werner, Hoffelner, Michael, Belaj, Ferdinand, Pirker, Teresa, Alajlani, Muaaz, Bauer, Rudolf, Pferschy-Wenzig, Eva-Maria, Saf, Robert, Weis, Robert
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes
antibacterial
anticancer activity
Cancer
Crystals
dihydropyridin-4(1H)-ones
Ethylenediaminetetraacetic acid
Fibroblasts
Gram-positive bacteria
Leukemia
Potash
Potassium
Structure
tetrahydropyridinylidene salts
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Zusammenfassung:Various 4-aminotetrahydropyridinylidene salts were treated with aldehydes in an alkaline medium. Their conversion to 5-substituted β-hydroxyketones in a one-step reaction succeeded only with an aliphatic aldehyde. Instead, aromatic aldehydes gave 5-substituted β-aminoketones or a single δ-diketone. The new compounds were characterized using spectroscopic methods and a single crystal structure analysis. Some of them showed anticancer and antibacterial properties.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules28196869