Synthesis and reactions of pyranoquinolines

358-3626-Aminocoumarins 1a-c are refluxed with ethyl benzoylacetate 2 in toluene to give benzoyl-N-(6'-coumarinyl)acetamides 3a-c, which on cyclisation with PPA afforded pyranoquinolines 4a-c. These are further converted into chloropyranoquinolines 5a-c using PCl5 and POCl3. These chloro derivatives are further treated separately, with sodium azide, anthranilic acid, o-phenylenediamine and benzoic hydrazide to obtain novel heterocyclic compounds, 9H-9-oxo-6-phenyl[10]pyrano[3 ,2-f]quinoline[1' ,5': 1,2] tetrazoles 6a-c, 10H, 15H-10, 15-dioxo-7-phenyl[11]pyrano[3,2-f]quinolino[1',2': 1,2] quinozolines 7a-c, 10H-10-oxo-7-phenyl[11]pyrano[3 ,2-f]quinolino[1 ',2': 1,2] benzimidazoles 8a-c and 9H-2,6-diphenyl-9- oxo [10]pyrano [3,2-f] quinolinof [1',2': 1,2]triazoles 9a-c, respectively