Abstract
4-Hydroxy-1-methyl-3-[E-3-(4-oxo-4H-chromen-3-yl)acryloyl]quinolin-2(1H)-one (3) was smoothly obtained via a one-pot aldol dehydration reaction of 3-acetyl-4-hydroxyquinolin-2(1H)-one with 3-formylchromone and was utilized to prepare miscellaneous triheterocyclic systems containing the quinolinone moiety. Both the α,β-unsaturated ketone side chain and the γ-pyrone ring in compound 3 were subjected to nucleophilic cyclization with certain 1,2- and 1,3-bifunctional N,N-, N,O-, N,C-, and O,C-nucleophiles under different reaction conditions. Many pyrazolinyl-, isoxazolinyl-, pyrimidinyl-, and pyridinylquinolinones bearing other six- or five-membered heterocyclic systems have been conveniently synthesized using more than one synthetic route.
Dedicated to the memory of the late Professor Sayed Ibrahim El-Nagdi.