Regiodivergent Ring-Expansion of Oxindoles to Quinolinones
Hendrik L. Schmitt, Den Martymianov, Ori Green, Tristan Delcaillau, Young Seo Park Kim, Bill Morandi
Abstract
The development of divergent methods to expedite structure-activity relationship studies is crucial to streamline discovery processes. We developed a rare example of regiodivergent ring expansion to access two regioisomers from a common starting material. To enable this regiodivergence, we identified two distinct reaction conditions for transforming oxindoles into quinolinone isomers. The presented methods proved to be compatible with a variety of functional groups, which enabled the late-stage diversification of bioactive oxindoles as well as facilitated the synthesis of quinolinone drugs and their derivatives.
Topics & Concepts
ChemistryStructural isomerRing (chemistry)Combinatorial chemistryDiversification (marketing strategy)StereochemistryOrganic chemistryBusinessMarketingAsymmetric Synthesis and CatalysisChemical synthesis and alkaloidsAdvanced Synthetic Organic Chemistry