Microwave-assisted Quaternization of Various Pyridine Derivatives and their Antibacterial Activity

In this study, reactions of quaternization under microwave heating of pyridine, [alpha]-picoline, pyridine-4-aldoxime, pyridine-2-aldoxime, nicotinamide, isonicotinamide and pyridoxal oxime with different electrophiles: 2-bromo-4'-nitroacetophenone, 2-amino-4-chloro-methylthiazole hydrochloride...

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Published inCroatica Chemica Acta Vol. 90; no. 3; p. 425
Main Authors Bušić, Valentina, Pavlović, Hrvoje, Roca, Sunčica, Vikić-Topić, Dražen, Gašo-Sokač, Dajana
Format Journal Article Paper
LanguageEnglish
Published Croatica Chemica Acta 01.12.2017
Hrvatsko kemijsko društvo
Subjects
antibacterial activity
Chemical properties
Chemical reactions
microwave synthesis
Microwaves
NMR
Observations
Pyridine
pyridine derivatives
quaternization
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Summary:In this study, reactions of quaternization under microwave heating of pyridine, [alpha]-picoline, pyridine-4-aldoxime, pyridine-2-aldoxime, nicotinamide, isonicotinamide and pyridoxal oxime with different electrophiles: 2-bromo-4'-nitroacetophenone, 2-amino-4-chloro-methylthiazole hydrochloride, methyl iodide, 1,3-diiodopropane and 1,3-dibromopropane are reported. The synthesis yield by microwave dielectric heating is improved and reaction time shortened compared to conventional heating. The structure of obtained molecules were analyzed and determined by 1D and 2D NMR spectroscopy methods, IR spectroscopy and mass spectrometry. The highest antibacterial activity against two Gram-positive and two Gram-negative bacteria strains has been found for 1-[2-(4-nitrophenyl)-2-oxoethyl]pyridinium bromide (2). Keywords: microwave synthesis, pyridine derivatives, antibacterial activity, NMR, quaternization.
Bibliography:185680
ISSN:0011-1643
1334-417X
DOI:10.5562/cca2937