Synthesis of Isoxazoline Derivatives through Boulton–Katritzky Rearrangement of 1,2,4-Oxadiazoles
- Authors: Palumbo Piccionello, A; Guarcello, A; Pace, A; Buscemi, S
- Publication year: 2013
- Type: Articolo in rivista (Articolo in rivista)
- OA Link: http://hdl.handle.net/10447/72957
Abstract
The base-induced rearrangement of 1,2,4-oxadiazoles into isoxazoline derivatives is reported. This represents the first example of a three-atom side-chain rearrangement that involves a saturated CCO side chain at C-3 of the oxadiazole. Nonaromatic 3-amino-isoxazoline derivatives are obtained in good yields. Interestingly, this reaction occurs through the rearrangement of aromatic oxadiazoles to form less stable bonds than those that are broken.