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

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Abstract

The base-induced rearrangement of 1,2,4-oxadiazoles intoisoxazoline derivatives is reported. This represents the firstexample of a three-atom side-chain rearrangement that involvesa saturated CCO side chain at C-3 of the oxadiazole. Nonaromatic 3-amino-isoxazoline derivatives are obtained ingood yields. Interestingly, this reaction occurs through therearrangement of aromatic oxadiazoles to form less stablebonds than those that are broken.
Original languageEnglish
Pages (from-to)1986-1992
Number of pages7
JournalEuropean Journal of Organic Chemistry
Volume2013
Publication statusPublished - 2013

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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