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

[Display omitted] 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 moie...

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Bibliographic Details
Published inMendeleev communications Vol. 34; no. 4; pp. 566 - 568
Main Authors Zhang, Yong, Bai, Junxue, Sun, Song
Format Journal Article
LanguageEnglish
Published Elsevier B.V 01.07.2024
Subjects
3,1-benzoxazines
alkene difunctionalization
cyclization
iodonium ion
organoiodine compounds
alkene difunctionalization
organoiodine compounds
3,1-benzoxazines
iodonium ion
cyclization
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Summary:[Display omitted] 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.
ISSN:0959-9436
DOI:10.1016/j.mencom.2024.06.032