Synthesis of 1-cyano-2-hydroxy-4-quinolizinones and corresponding 5-cyano-4-hydroxy-2-pyridones. Part 187: Synthesis of heterocycles. Part 9: Quinolizines and Indolizines.
Active malonic esters condense with 2-pyridylacetonitrile giving 1-cyano-3-substituted 2-hydroxyquinolizin-4-ones. Catalytic hydrogenation of the resulting products led to the corresponding 1-cyano-3-substituted-2-hydroxy-6.7.8.9-tetrahydroquinolizin-4-ones. On the other hand, condensation of the active malonic esters with beta-aminocrotononitrile afforded 5-cyano-3-substituted-4-hydroxy-6-methylpyridine-2-ones. The IR and NMR data are reported.
D007212:Indolizines / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D011728:Pyridones / Q000138:chemical synthesis; D011807:Quinolizines / Q000138:chemical synthesis*
D007212:Indolizines; D011728:Pyridones; D011807:Quinolizines