Reactions with 2(1H)-quinolinone and coumarine derivatives: New routes to polysubstituted 2(1H)-quinolinone and coumarine derivatives

Article abstract of DOI:10.1246/bcsj.68.905

Whereas 2H-pyrano[3,2-c[quinoline-2,5(6H)-dione (2a) or 3-acetyl-1-methyl-2(1H)-quinolinone (3a) reacted with the benzylidenenitriles 1a-f or a mixture of either malononitrile or ethyl cyanoacetate and aromatic aldehydes in ethanol/piperidine to give 4H-pyran derivatives 8, the reaction of 2b,c or 3b,c with the same reagents afforded 4,6-dihydro-5H-pyrano[3,2-c]quinolin-5-ones 11. Compounds 11 were also prepared from 1a-f and 3d,e,f. Reaction of pyrano[3,2-c]coumarin 2d with 1a yielded 6H,11H-[2]benzopyrano[4,3-c]-[1]benzopyran-6,11-dione (15). Treatment of 17 with aqueous potassium cyanide or hydroxylamine afforded the 2(1H)-quinolinone derivatives 19 and 20 respectively.