Synthesis of some new quinoline derivatives: new routes to synthesize polysubstituted 2(1H)-quinolone derivatives.

Reaction of 4-hydroxyquinolines 1a,b or 1c,d with the ylidenenitriles 2b-g and 2h,c yielded pyranoquinolines 6 and 9, respectively. 4-Anilinoquinoline 10 reacted with 2a,e to give pyridoquinolines 12. Treating of 1a or 14 with SO2Cl2 gave 3-dichloroacetyl derivative 15. Compound 15 reacted with KCN/H2O and NaN3 to give furoquinoline 16 and the tetrazole 18, respectively. Reaction of 1a, b, f with a mixture of phenyl isothiocyanate and glycine gave pyranoquinoline 22. This compound reacted with chloroacetic acid to yield thiazolidinones 23. Pyranoquinolines 27 were synthesized either from the reaction of 1c,d with enamine 24 or reaction of 1e,f with hippuric acid. Condensation of 1c,d with the enamine 25 gave azlactone 28. The latter compound reacted with 4-aminoantipyrine and 2-aminopyridine to give the imidazole derivatives 30.