Dieckmann Condensation of Ugi <i>N</i>-Acylamino Amide Product: Facile Access to Functionalized 2,2-Disubstituted Indolin-3-ones
Yong Li, Jia Xu, Liu‐Jun He, Yafei Luo, Jiang Ping Meng, Dianyong Tang, Hongyu Li, Zhong‐Zhu Chen, Zhigang Xu
Abstract
Structurally unique 2,2-disubstituted indolin-3-ones with a quaternary carbon center have been constructed through a novel C–C bond formation at the C3 position of Ugi N-acylamino amide adducts employing an organic base-mediated Dieckmann condensation. This facile, flexible protocol can be fine-tuned to construct drug-like pyrazino[1,2-a]indole fragments with the same quaternary carbon center only through the variation of the acid part in Ugi input. This novel and expeditious methodology has a broad scope and can rapidly generate the drug-like indolin-3-one core.
Topics & Concepts
ChemistryAmideAdductCombinatorial chemistryQuaternary carbonIndole testCondensationCondensation reactionStereochemistryOrganic chemistryCatalysisEnantioselective synthesisPhysicsThermodynamicsMulticomponent Synthesis of HeterocyclesSynthesis of Organic CompoundsChemical Synthesis and Analysis