Synthesis and biological effects of new derivatives of azines incorporating coumarin

✍ Scribed by Fatima Al-Omran; Abdel-Zaher A. Elassar; Adel Abou El-Khair

• Book ID: 102339993
• Publisher: Journal of Heterocyclic Chemistry
• Year: 2003
• Tongue: English
• Weight: 80 KB
• Volume: 40
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570400208

✦ Synopsis

Abstract

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)‐2__H__‐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]‐2__H__‐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.