Substituted Quinolinones, Part 12: Heterocyclization Reactions of 3‐(3‐Chromonyl)acryloylquinolinone with Some Bifunctional Nucleophiles

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.

Keywords:

• chromone
• nucleophilic cycloaddition
• quinolinone
• α,β‐unsaturated ketone

Acknowledgments

The authors thank E. A. Mohamed and M. M. Ismail of the Chemistry Department, Faculty of Education, Ain Shams University, and Akram Hassan, of the Ministry of Education, for their valuable services and facilities.

Notes

Dedicated to the memory of the late Professor Sayed Ibrahim El‐Nagdi.