Abstract
Some new 2-alkoxy-3-cyano-4,6-diarylpyridines
3,
4 were synthesized by condensation of different α,β-unsaturated ketones
1 with malononitrile
2, followed by cyclization in sodium alkoxide/alcohol system. Lewis acid-catalyzed reaction of
4 with hydrazine afforded the corresponding 1
H-pyrazolo[3,4-
b]pyridines
5. The potency of the results as antimicrobial agents has been evaluated. The structure of the newly prepared compounds was assessed by microanalysis, IR and NMR spectra. Molecular mechanics (MM2) and semiemperical (AM1) molecular orbital calculations have been performed for the most biologically active compounds
5b and
c to get insight into their molecular structures and to learn more about their stable molecular conformations.
Lewis acid-catalyzed reaction of hydrazine (99%) with 2-methoxy-3-cyano-4,6-diarylpyridines afforded the corresponding 1
H-pyrazolo[3,4-
b]pyridines under mild conditions.