Formation of a tetracyclic isoquinoline derivative by rearrangement of a [(bromophenyl)butyryl]oxazolidinone

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Abstract

Treatment of 3-[4-(2-bromophenyl)-2-phenylbutyryl]-4,4-dimethyloxazohdin-2-one with LDA in THF launched a domino rearrangement sequence ending in the assembly of a tetracyclic cyclopentaoxazolo[3,2-b]isoquinolin-6-one derivative. Two mechanisms involving an S(RN)1-type process were proposed. EPR spectroscopic and C-13-labelling experiments suggested that both were operative. (C) Wiley-VCH Verlag GmbH & Co.

Original languageEnglish
Pages (from-to)1059-1063
Number of pages5
JournalEuropean Journal of Organic Chemistry
DOIs
Publication statusPublished - Feb 2007

Keywords

  • rearrangement
  • cyclisation
  • heterocycles
  • radical ions
  • EPR spectroscopy
  • NUCLEOPHILIC-SUBSTITUTION
  • CHLORANILINES
  • CYCLIZATIONS
  • DIANIONS

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