Iron(III)-Mediated Nucleophilic Cascade Cyclization of Tertiary Enamides with Diselenides for the Construction of 3-Seleno-2-pyridones
Xin‐Ming Xu, Jiping Wang, Xiaoxu Chen, Zhongyuan Zhao, Qian Liu, Miao Tian, Kai Sun
Abstract
-propiolyl enamides with various diselenides was developed, which provides an efficient way to construct seleno-heterocycles. A mechanism study shows that the cascade process involves the selective addition of diselenides to the C≡C bond generating a seleniranium ion, followed by an intramolecular nucleophilic attack of enaminic carbon of tertiary enamide. Utilizing this protocol, a variety of 3-seleno-2-pyridones were successfully synthesized featuring good functional group compatibility and simple operation.
Topics & Concepts
ChemistryNucleophileCascadeSeleniumCombinatorial chemistryMedicinal chemistryStereochemistryCatalysisOrganic chemistryChromatographyOrganoselenium and organotellurium chemistrySulfur-Based Synthesis TechniquesSynthesis and biological activity