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...

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Bibliographic Details
Published in:Journal of heterocyclic chemistry 2003-03, Vol.40 (2), p.249-254
Main Authors: Al-Omran, Fatima, Elassar, Abdel-Zaher A., El-Khair, Adel Abou
Format: Article
Language:English
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Summary: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.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.5570400208