Phase-transfer catalyzed Michael/ammonolysis cascade reactions of enaminones and olefinic azlactones: a new approach to structurally diverse quinoline-2,5-diones

Michael/ammonolysis cascade reactions between cyclohexane-1,3-dione-derived enaminones and olefinic azlactones via phase-transfer catalysis have been developed. This method provides rapid access to a suite of architecturally complex and diverse quinoline-2,5-diones bearing a secondary amide group at the C-3 position in moderate to excellent yields (53–94%) and with excellent diastereoselectivities (>99 : 1 dr in most cases). The achievement of a preparative-scale reaction and the diverse product derivatization that can be obtained highlight the application potential of this protocol both in academic and industrial settings. An investigation of the reaction mechanism implies that tetrabutylammonium hydroxide may be the actual catalyst during this cascade reaction.