Rapid Access to Functionalized 2-Quinolinones and Coumarins by Direct Coupling of 2-Alkynyl-anilines/phenols and Diazo Ketones

The microwave-assisted direct coupling of 2-alkynyl-anilines/phenols and diazo ketones through Wolff rearrangement, intramolecular 1,4-addition and nucleophile assisted fragmentation to synthesize functionalized 2-quinolinones and coumarins are reported. This one-pot manipulation features a short reaction time, high synthetic efficiency and broad substrate scope. We have developed the strategies for synthesizing 2-quinolinones and coumarins by directly coupling 2-alkynyl-anilines/phenols and diazo ketones. The features of our work include: 1) several transformations are telescoped into one-pot manipulations to maximize synthetic efficiency; 2) the reactions allow for the incorporation of several functional groups into the medicinally privileged architectures.image