FeCl2‐Catalyzed Rearrangement of Aryl Peroxyoxindole into 1,3‐Benzooxazin‐4‐One

We report an FeCl2‐catalyzed radical rearrangement of aryl peroxyoxindoles into 1,3‐benzooxazin‐2‐ones to obtain a variety of aryl substituted 1,3‐benzooxazin‐4‐ones in moderate to good yields. Mechanistically, this skeletal rearrangement of peroxyoxindoles proceeded via radical pathway and was well...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2023-02, Vol.365 (4), p.515-521
Main Authors: Mohanta, Nirmala, Paramita Samal, Pragnya, Krishnamurty, Sailaja, Gnanaprakasam, Boopathy
Format: Article
Language:English
Subjects:
1,3-Benzooxazin-4-one
Aromatic compounds
FeCl2
Iron chlorides
Peroxyoxindole
Rearrangement
Ring expansion
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Summary:We report an FeCl2‐catalyzed radical rearrangement of aryl peroxyoxindoles into 1,3‐benzooxazin‐2‐ones to obtain a variety of aryl substituted 1,3‐benzooxazin‐4‐ones in moderate to good yields. Mechanistically, this skeletal rearrangement of peroxyoxindoles proceeded via radical pathway and was well supported with a series of experimental findings and DFT studies.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202201308