Inverse Electron Demand Diels Alder Reaction of Aza- o -Quinone Methides and Enaminones: Accessing 3-Aroyl Quinolines and Indeno[1,2- b ]quinolinones.

We have developed a Diels Alder cycloaddition route toward 3-aroyl quinolines from enaminones and in situ generated aza- o -quinone methides. The reaction was found to be general with a range of substituted enaminones and aza- o -quinone methides, and we could validate the applicability of the methodology in gram scale. We also demonstrated a one-pot strategy toward 3-acyl quinolines starting from the corresponding aliphatic ketones. Finally, we utilized the 3-aroyl quinolines for synthesizing indeno[1,2- b ]quinolinones via a Pd-catalyzed dual C-H activation approach.