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 supported with a series of experimental findings and DFT studies.

Automated summary

We describe a FeCl2-catalyzed radical rearrangement of aryl peroxyoxindoles to obtain aryl substituted 1,3-benzooxazin-4-ones in moderate to good yields. Mechanistically, this rearrangement proceeds via a radical pathway and is supported by experimental findings and DFT studies.