6533b829fe1ef96bd128ab1b

RESEARCH PRODUCT

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

Antonio Palumbo-piccionelloSilvestre BuscemiAndrea PaceAnnalisa Guarcello

subject

chemistry.chemical_compoundChemistryStereochemistryOrganic ChemistrySide chainOxadiazoleAromaticityPhysical and Theoretical ChemistrySigmatropic reactionCarroll rearrangementCope rearrangement

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
2013-02-07European Journal of Organic Chemistry
https://doi.org/10.1002/ejoc.201201308