Hydroxyaryl-isoxazoles: Synthesis and related studies

Academic Article

Abstract

  • The oximes of 2′-hydroxyacetophenone, 2′-hydroxypropiophenone, 1′-hydroxy-2-acetonaphthone, or 2′-hydroxy-3-phenylpropiophenone were trilithiated with excess lithium diisopropylamide, and the resulting trianion-type intermediates were condensed with a variety of aromatic esters followed by acid cyclization to substituted hydroxyaryl-isoxazoles. Since all of the atoms giving rise to the isoxazole ring are in place in the precyclization intermediate, the formation of a single bond results in a single isoxazole isomer and an unequivocal synthesis. Compounds were characterized by absorption spectra, and the potential of these compounds to undergo excited state intramolecular proton transfer was investigated.
  • Published In

  • Chemist  Journal
  • Author List

  • Williams AR; Finefrock AE; Townsend JD; Angel AJ; Hurst DR; Rampey ME; Halkyard CE; Studer-Martinez SL; Beam CF
  • Start Page

  • 7
  • End Page

  • 11
  • Volume

  • 75
  • Issue

  • 4