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Studies with quinolines: New synthetic routes to 4 H ,5 H ,6 H ,9 H ‐benzo[ ij ]pyrano[2,3‐ b ]quinolizine‐8‐one, 4 H ‐pyrano[2,3‐ b ]pyridine, 2 H ‐pyran‐2‐one and pyranopyridoquinoline derivatives
Author(s) -
ElTaweel Fathy Mohamad Abdel Aziz
Publication year - 2005
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.5570420529
Subject(s) - chemistry , quinoline , pyran , hippuric acid , pyridine , medicinal chemistry , stereochemistry , dimethylformamide , organic chemistry , solvent , urine , biochemistry
Several new benzo[ ij ]pyrano[2,3‐ b ]quinolizine‐8‐ones 5 and 4 H ‐pyrano[2,3‐ b ]pyridine 8 derivatives were synthesized from 4‐hydroxyquinolines 1 . Reacting 3‐acetyl‐4‐hydroxy‐1‐phenyl‐1 H ‐quinoline‐2‐one with dimethylformamide dimethylacetal afforded 3‐(3‐Dimethylarnino‐acryloyl)‐4‐hydroxy‐1‐phenyl‐1 H ‐quinolin‐2‐one 9 . This reacted with hippuric acid and diethyl 3‐oxoglutarate to give 2 H ‐pyran‐2‐one 13 and pyranopyridoquinoline 17 respectively.