Efficient access to novel tetra- and pentacyclic dihydroquinolin-2-ones by catalyst-free domino Knoevenagel hetero-Diels-Alder reactions from N-(2-formylphenyl)-N-methylcinnamamides and cyclic 1,3-dicarbonyls in water

An efficient catalyst-free synthesis of novel annulated hybrid derivatives of two known scaffolds, dihydroquinolinone and pyranopyranone, pyranopyrimidinedione, pyranocoumarin or chromenone is described. N-(2-Formylphenyl)-N-methylcinnamamides underwent a one-pot domino Knoevenagel hetero-Diels-Alder reaction with dimedone, N,N-dimethylbarbituric acid, 1,3-indanedione, 4-hydroxycoumarins and 4-hydroxy-6-methyl-2H-pyran-2-one in water, affording the desired tetra and pentacyclic pyranoquinolinones in excellent yields.