Synthesis of Seleno Oxindoles via Iodine-Induced Radical Cyclization of N-Arylacrylamides with Diorganyl Diselenides

Hongmei Jiang; Haicheng Shen; Cehua Li; Zheng Jin; Yanxue Shang; Yufeng Chen; Min Yi; Juan Du; Qing-Wen Gui

doi:10.1055/a-1739-5042

Synthesis, Table of Contents

Synthesis 2022; 54(11): 2669-2676
DOI: 10.1055/a-1739-5042

paper

Synthesis of Seleno Oxindoles via Iodine-Induced Radical Cyclization of N-Arylacrylamides with Diorganyl Diselenides

Hongmei Jiang

^aCollege of Chemistry and Materials Science, Hunan Agricultural University, Changsha 410128, P. R. of China

,

Haicheng Shen

^aCollege of Chemistry and Materials Science, Hunan Agricultural University, Changsha 410128, P. R. of China

,

Cehua Li

^aCollege of Chemistry and Materials Science, Hunan Agricultural University, Changsha 410128, P. R. of China

,

Zheng Jin

^aCollege of Chemistry and Materials Science, Hunan Agricultural University, Changsha 410128, P. R. of China

,

Yanxue Shang

^aCollege of Chemistry and Materials Science, Hunan Agricultural University, Changsha 410128, P. R. of China

,

Yufeng Chen

^aCollege of Chemistry and Materials Science, Hunan Agricultural University, Changsha 410128, P. R. of China

,

Min Yi

^aCollege of Chemistry and Materials Science, Hunan Agricultural University, Changsha 410128, P. R. of China

,

Juan Du∗

^aCollege of Chemistry and Materials Science, Hunan Agricultural University, Changsha 410128, P. R. of China

^bInternational Joint Research Centre for Molecular Science, College of Chemistry and Environmental Engineering, Shenzhen University, Shenzhen 518060, P. R. of China

,

Qing-Wen Gui ∗

^aCollege of Chemistry and Materials Science, Hunan Agricultural University, Changsha 410128, P. R. of China

^cHunan Optical Agriculture Engineering Technology Research Center, Changsha 410128, P. R. of China

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Abstract

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Abstract

A mild, radical cascade cyclization of N-arylacrylamides with diselenides for the preparation of oxindoles via iodine oxidation is disclosed that provides an environmentally friendly process for the construction of C–Se bonds. Twenty-five examples of N-arylacrylamide substrates were investigated, and excellent yields were achieved. The tandem cyclization of acrylamide with diphenyl disulfide was also applicable under the same conditions.

Key words

seleno oxindoles - iodine-induced - radical reaction - C–Se bond - cyclization

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