Iodocyclization of olefinic amides with acetoxybenziodoxolone and NaI toward 4-iodomethylated benzoxazines

Iodocyclization of N-(2-alkenylphenyl)carboxamides with acetoxybenziodoxolone/NaI system gives 4-iodomethyl- 4H-3,1-benzoxazines with high efficiency. The process is triggered by the oxidation of NaI with acetoxybenziodo- xolone to afford iodine cation which is added to alkene moiety to form iodonium species, and the ultimate intra- molecular nucleophilic addition generates the final products.