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).