AbstractThe 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.