Synthesis and biological effects of new derivatives of azines incorporating coumarin

New synthetic routes for triazolopyridine, pyridopyrimidine, pyridotriazine, imidazopyridine and pyri-dazine derivatives incorporating a coumarin moiety with interesting biological activities are reported. Reactions of the 2-oxo-4-(2-dimethylaminoethenyl)-2H-chromene-3-carbonitrile (4) and 2-amino-4-(2-dimethylaminoethenyl)quinoline-3-carbonitrile (5) with benzotriazol-1-yl-acetic acid hydrazide (6) affords the substituted [1,2,4]triazolo[1,5-a]pyrido[3,4-c]coumarines 9 and quinoline 12, respectively. Treatment of 4 with 2-amino-pyridine, glycine, urea, 3-aminocrotononitrile or cyanothioacetamide affords 14–18, respectively. Treatment of 3-amino-3,4-dihydro-4-imino-chromeno[3,4-c]pyridin-5-one (10) with α-chloro-acetylacetone affords pyridotriazine derivative 21. Compound 4 was also coupled with benzenediazonium chloride to afford 2-oxo-4-[2-oxo-1-(phenyl-hydrazono)-ethyl]-2H-chromene-3-carbonitrile 25. Treatment of the latter product with malononitrile afforded the 1-phenyl-3-(3′-Cyano-2′-oxo-coumarin-4′-yl)-6-oxo-pyridazine-5-carbonitrile (27). The structures of the newly synthesized compounds have been established on the basis of analytical and spectral data.