Radical Annulation of 2-Cyanoaryl Acrylamides via C═C Double Bond Cleavage: Access to Amino-Substituted 2-Quinolones
Wen‐Jin Xia, Tai‐Gang Fan, Zhiwei Zhao, Xin Chen, Xiangxiang Wang, Ya‐Min Li
Abstract
A novel annulation of 2-cyanoaryl acrylamides via C═C double bond cleavage has been developed for facile and efficient access to a broad spectrum of functionalized 4-amino-2-quinolones, which are important N-heterocycles. In this transformation, the solvent THF is demonstrated to play a crucial role, and the addition of alkyl radicals to nitrile, 1,5-hydride shift, and cleavage of the C–C bond are involved in the mechanism.
Topics & Concepts
AnnulationChemistryBond cleavageCleavage (geology)NitrileRadicalHydrideDouble bondMedicinal chemistryCombinatorial chemistryStereochemistryAlkylOrganic chemistryCatalysisFracture (geology)Geotechnical engineeringHydrogenEngineeringRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques