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
a   College of Chemistry and Materials Science, Hunan Agricultural University, Changsha 410128, P. R. of China
,
Haicheng Shen
a   College of Chemistry and Materials Science, Hunan Agricultural University, Changsha 410128, P. R. of China
,
Cehua Li
a   College of Chemistry and Materials Science, Hunan Agricultural University, Changsha 410128, P. R. of China
,
Zheng Jin
a   College of Chemistry and Materials Science, Hunan Agricultural University, Changsha 410128, P. R. of China
,
Yanxue Shang
a   College of Chemistry and Materials Science, Hunan Agricultural University, Changsha 410128, P. R. of China
,
Yufeng Chen
a   College of Chemistry and Materials Science, Hunan Agricultural University, Changsha 410128, P. R. of China
,
Min Yi
a   College of Chemistry and Materials Science, Hunan Agricultural University, Changsha 410128, P. R. of China
,
Juan Du
a   College of Chemistry and Materials Science, Hunan Agricultural University, Changsha 410128, P. R. of China
b   International Joint Research Centre for Molecular Science, College of Chemistry and Environmental Engineering, Shenzhen University, Shenzhen 518060, P. R. of China
,
Qing-Wen Gui
a   College of Chemistry and Materials Science, Hunan Agricultural University, Changsha 410128, P. R. of China
c   Hunan Optical Agriculture Engineering Technology Research Center, Changsha 410128, P. R. of China
› Institutsangaben
This work was financially supported by the Hunan Province Science Foundation for Youths (2020JJ4035) and Double First-Class Construction Project of Hunan Agricultural University (SYL2019064, SYL2019063), the Basic Research Foundation of China Tobacco Yunnan Industrial Corporation (11700167), Outstanding postdoctoral Innovative Talents Program of Science and Technology Innovation Talents Program of Hunan Province (2021RC2079) and Foundation of Hunan Provincial Key Laboratory of Crop Germplasm Innovation and Resource Utilization (18KFXM07).


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.

Supporting Information



Publikationsverlauf

Eingereicht: 03. November 2021

Angenommen: 13. Januar 2022

Accepted Manuscript online:
13. Januar 2022

Artikel online veröffentlicht:
17. März 2022

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