Synthesis of Imidazoles and Oxazoles via a Palladium-Catalyzed Decarboxylative Addition/Cyclization Reaction Sequence of Aromatic Carboxylic Acids with Functionalized Aliphatic Nitriles
Ling Dai, Shuling Yu, Ningning Lv, Xuanzeng Ye, Yinlin Shao, Zhongyan Chen, Jiuxi Chen
Abstract
We herein report an efficient approach for the assembly of multiply substituted imidazoles and oxazoles in a single-step manner. These transformations are based on a decarboxylation addition and annulation of readily accessible aromatic carboxylic acids and aliphatic nitriles and exhibit good functional group compatibility and a high step economy. The reaction is scalable, and as-prepared products could be transformed into practical skeletons. Importantly, the late-stage derivatization of Momelotinib highlights the potential utility of this methodology.
Topics & Concepts
ChemistryDecarboxylationAnnulationDerivatizationCatalysisFunctional groupPalladiumCombinatorial chemistryOrganic chemistryAmideReaction conditionsPolymerHigh-performance liquid chromatographyCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsSynthesis and Biological Evaluation