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

Yong Zhang 1
Yong Zhang
, 
Junxue Bai 2
Junxue Bai
, 
Song Sun 2
Song Sun
1 Suzhou Industrial Park Institute of Services and Outsourcing, Suzhou, Jiangsu, China
2 School of Petrochemical Engineering, Changzhou University, Changzhou, China
10.1016/j.mencom.2024.06.032
Published 2024-06-19
Communication , Volume 34, Issue 4, 566-568
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Zhang Y., Bai J., Sun S. Iodocyclization of olefinic amides with acetoxybenziodoxolone and NaI toward 4-iodomethylated benzoxazines // Mendeleev Communications. 2024. Vol. 34. No. 4. pp. 566-568.
GOST all authors (up to 50) Copy
Zhang Y., Bai J., Sun S. Iodocyclization of olefinic amides with acetoxybenziodoxolone and NaI toward 4-iodomethylated benzoxazines // Mendeleev Communications. 2024. Vol. 34. No. 4. pp. 566-568.
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TY - JOUR
DO - 10.1016/j.mencom.2024.06.032
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.06.032
TI - Iodocyclization of olefinic amides with acetoxybenziodoxolone and NaI toward 4-iodomethylated benzoxazines
T2 - Mendeleev Communications
AU - Zhang, Yong
AU - Bai, Junxue
AU - Sun, Song
PY - 2024
DA - 2024/06/19
PB - Mendeleev Communications
SP - 566-568
IS - 4
VL - 34
ER -
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@article{2024_Zhang,
author = {Yong Zhang and Junxue Bai and Song Sun},
title = {Iodocyclization of olefinic amides with acetoxybenziodoxolone and NaI toward 4-iodomethylated benzoxazines},
journal = {Mendeleev Communications},
year = {2024},
volume = {34},
publisher = {Mendeleev Communications},
month = {Jun},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.06.032},
number = {4},
pages = {566--568},
doi = {10.1016/j.mencom.2024.06.032}
}
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Zhang, Yong, et al. “Iodocyclization of olefinic amides with acetoxybenziodoxolone and NaI toward 4-iodomethylated benzoxazines.” Mendeleev Communications, vol. 34, no. 4, Jun. 2024, pp. 566-568. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.06.032.

Keywords

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

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.

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