The article presents a regidivergent method for the ring expansion of oxindoles to quinolinones, a rare example of regioselective synthesis from a common starting material. The authors identified two distinct reaction conditions, one using LiHMDS and the other using AgBF4, to achieve the desired products. The method is compatible with various functional groups and can be applied to late-stage diversification of bioactive compounds and the synthesis of quinolinone drugs and their derivatives. The mechanism of the reaction involves the activation of strong bonds and the identification of complementary reaction conditions, which are crucial for regidivergence. The study demonstrates the potential of this approach in streamlining structure-activity relationship studies and the discovery of novel pharmaceuticals.The article presents a regidivergent method for the ring expansion of oxindoles to quinolinones, a rare example of regioselective synthesis from a common starting material. The authors identified two distinct reaction conditions, one using LiHMDS and the other using AgBF4, to achieve the desired products. The method is compatible with various functional groups and can be applied to late-stage diversification of bioactive compounds and the synthesis of quinolinone drugs and their derivatives. The mechanism of the reaction involves the activation of strong bonds and the identification of complementary reaction conditions, which are crucial for regidivergence. The study demonstrates the potential of this approach in streamlining structure-activity relationship studies and the discovery of novel pharmaceuticals.