Oxidative Difunctionalization of 2?Amino?4H?pyrans in Iodobenzene Diacetate and N?Chlorosuccinimide: Reactivity, Mechanistic Insights, and DFT Calculations

摘要

Oxidative difunctionalization of 2-amino-4H-pyransnwas accomplished with iodobenzene diacetate (IBD) and Nchlorosuccinimiden(NCS) reagents in alcoholic medium. 2-Amino-n4H-pyrans undergo geminal dialkoxylation with the migration of annamino group (1a,b, 2a−i, 3a,b, and 4) in IBD, whereas with NCSnaddition of both chlorine and alkoxy groups takes place across thenchromene double bond (6a−i).