Synthesis of oxindoles and benozfuranones via oxidation of 2-heterocyclic BMIDAs

Ciaran Paul Seath, James W. B. Fyfe, John J. Molloy, Allan J. B. Watson

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

The synthesis of functionalized oxindoles and benzofuranones via oxidation of 2-BMIDA indoles and benzofurans, respectively, is described. Interconversion of boron species (BMIDA→BF3K) was necessary to enable oxidation and overcome boronic acid stability issues associated with a difficult BMIDA hydrolysis. Overall, a robust process was developed that allowed access to a small library of oxindole and benzofuranone products and facilitated the step-efficient synthesis of biologically-active compounds containing the oxindole pharmacophore.
Original languageEnglish
Pages (from-to)891-898
JournalSynthesis
Volume49
Issue number4
Early online date12 Aug 2016
DOIs
Publication statusPublished - Feb 2017

Keywords

  • Boron
  • Oxidation
  • Heterocycles
  • Lactams
  • Lactones
  • Functionalized oxindoles synthesis
  • Benzofuranones
  • Boronic acid stability
  • Oxindole pharmacophore

Fingerprint

Dive into the research topics of 'Synthesis of oxindoles and benozfuranones via oxidation of 2-heterocyclic BMIDAs'. Together they form a unique fingerprint.

Cite this