Copper-Catalyzed N–O Cleavage of α,β-Unsaturated Ketoxime Acetates toward Structurally Diverse Pyridines
Lei Zhang, Jindian Duan, Gaochen Xu, Xiaojuan Ding, Yiyang Mao, Binsen Rong, Ning Zhu, Zheng Fang, Zhenjiang Li, Kai Guo
Abstract
The copper-catalyzed [4 + 2] annulation of α,β-unsaturated ketoxime acetates with 1,3-dicarbonyl compounds for the synthesis of three classes of structurally diverse pyridines has been developed. This method employs 1,3-dicarbonyl compounds as C2 synthons and enables the synthesis of multifunctionalized pyridines with diverse electron-withdrawing groups in moderate to good yields. The mechanistic investigation suggests that the reactions proceed through an ionic pathway.
Topics & Concepts
ChemistrySynthonAnnulationCatalysisCleavage (geology)CopperIonic bondingOrganic chemistryMedicinal chemistryCombinatorial chemistryIonFracture (geology)Geotechnical engineeringEngineeringCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsClick Chemistry and Applications