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

Oxidative difunctionalization of 2-amino-4H-pyrans was accomplished with iodobenzene diacetate (IBD) and N-chlorosuccinimide (NCS) reagents in alcoholic medium. 2-Amino-4H-pyrans undergo geminal dialkoxylation with the migration of an amino group (1a,b, 2a–i, 3a,b, and 4) in IBD, whereas with NCS addition of both chlorine and alkoxy groups takes place across the chromene double bond (6a–i).