Synthesis 2022; 54(02): 411-420
DOI: 10.1055/s-0040-1719833
paper

Intramolecular Chalcogenylation of Isooxazolines Mediated by PhICl2 and Diorganyl Disulfides or Diselenides

Dongke Zhang
a   Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China
,
Jingran Zhang
a   Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China
,
Xiaoxian Li
a   Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China
,
Zhenyang Yu
a   Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China
,
Yadong Li
a   Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China
,
Fengxia Sun
b   College of Chemical and Pharmaceutical Engineering, Hebei University of Science and Technology; Hebei Research Center of Pharmaceutical and Chemical Engineering, Shijiazhuang 050018, P. R. of China
,
Yunfei Du
a   Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China
› Author Affiliations
Y. Du acknowledges the National Natural Science Foundation of China (#22071175) and F. Sun acknowledges the National Natural Science Foundation of China (U20A20144) for financial supports.


Abstract

Reactive organosulfenyl chlorides (ArSCl) or selenenyl chlorides (ArSeCl), generated in situ from the reaction of PhICl2 with diorganyl disulfides or diselenides, enable the intramolecular oxidative cyclization/chalcogenylation of β,γ-unsaturated oximes, leading to the formation of a series of chalcogenylated isooxazolines in good to excellent yield.

Supporting Information



Publication History

Received: 26 July 2021

Accepted after revision: 24 August 2021

Article published online:
22 September 2021

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