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

Abstract

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.