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Azachalcones. Part 2: Reactions of 3,3-diazachalcones.

1,3-Di(3-pyridyl)-2-propen-1-one (1) react with malononitrile in presence of ammonium acetate to afford 2-amino-3-cyano-4, 6-di(3-pyridyl)pyridine (2), which was converted to the nicotinamide derivative 3 by hydrolysis with alkali. In a similar way, 1 react with ethyl cyanoacetate to give 3-cyano-4,6-(3-pyridyl)-2-pyridone (4). Treating of 1 with hydroxylamine hydrochloride afforded the oxime 5 which upon reaction with alkyl- or aryl-isocyanates gave the oxime carbamates 6. Reaction of thiourea and hydrazines with 1 gave the thiopyrimidine 7 and the pyrazolines 8, respectively. The structure of the obtained compounds was confirmed according to their IR and UV spectra. The antimicrobial activity of the synthesized compounds against several microorganisms is presented.[1]

References

  1. Azachalcones. Part 2: Reactions of 3,3-diazachalcones. Attia, A., Michael, M. Die Pharmazie. (1982) [Pubmed]
 
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