A facile eco-friendly three-component protocol for the regio- and stereoselective synthesis of functionalized trans-dihydrofuro[3,2-c]-quinolin-4(2H)-ones

Abstract

A series of novel trans-2-aroyl-5-methyl-3-aryl-3,5-dihydrofuro[3,2-c]quinolin-4(2H)-ones has been synthesized in good yields from the three-component reaction of 4-hydroxy-1-methyl-2(1H)-quinolinone, aromatic aldehydes and 1-(2-oxo-2-arylethyl)pyridinium bromides in the presence of a catalytic amount of triethylamine in water under microwave irradiation. This green domino transformation, generating one C–O and two C–C bonds, presumably proceeds via generation of α,β-unsaturated diketone and ylide, Michael addition and intramolecular cyclisation.