Premium
Synthesis and biological effects of new derivatives of azines incorporating coumarin
Author(s) -
AlOmran Fatima,
Elassar AbdelZaher A.,
ElKhair Adel Abou
Publication year - 2003
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570400208
Subject(s) - chemistry , malononitrile , pyridazine , moiety , acetylacetone , pyridine , coumarin , quinoline , cyanoacetamide , hydrazide , medicinal chemistry , acetic acid , pyrimidine , organic chemistry , stereochemistry , catalysis
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.