6533b7d9fe1ef96bd126bdb7

RESEARCH PRODUCT

Synthesis of Isoxazoline Derivatives through Boulton–Katritzky Rearrangement of 1,2,4-Oxadiazoles

Antonio Palumbo PiccionelloAnnalisa GuarcelloAndrea PaceSilvestre Buscemi

subject

Synthetic methods Rearrangement Heterocycles AromaticitySettore CHIM/06 - Chimica Organica

description

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.

yearjournalcountryeditionlanguage
2013-01-01
10.1002/ejoc.201201308http://hdl.handle.net/10447/72957