Y. Zhang, J. Bai, S. Sun, “Iodocyclization of olefinic amides with acetoxybenziodoxolone and NaI toward 4-iodomethylated benzoxazines”, Mendeleev Commun., 2024, Volume 34, Issue 4,Pages <nobr>566

Communications

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

Y. Zhang^a, J. Bai^b, S. Sun^b

^a Suzhou Industrial Park Institute of Services and Outsourcing, Suzhou, Jiangsu, China
^b School of Petrochemical Engineering, Changzhou University, Changzhou, China

Abstract: 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.

Keywords: iodonium ion, alkene difunctionalization, 3,1-benzoxazines, organoiodine compounds, cyclization.

Language: English

DOI: 10.1016/j.mencom.2024.06.032

	*Supplementary materials:*
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