Synthesis of the Disubstituted Maleic Anhydride Frame Using a Novel Tandem Radical-Polar Reaction

Mariella Pattarozzi, Franco Ghelfi, Fabrizio Roncaglia, Ugo M. Pagnoni, Andrew F. Parsons

Research output: Contribution to journalArticlepeer-review

Abstract

An unreported 5-endo-trig atom-transfer radical cyclization of cyclic N-alpha-dichloroacyl-ketene-N,S-acetals, which evolves as a tandem radical-polar process, is described. The reaction, which is carried out in the presence of a Cu(I) complex catalyst (10 mol%) and an inorganic base (i.e., carbonate), can be exploited as the key step for a novel, short, and versatile synthesis of the 3,4-disubstituted maleic anhydride nucleus.

Original languageEnglish
Pages (from-to)2172-2176
Number of pages5
JournalSynlett
Issue number13
DOIs
Publication statusPublished - 13 Aug 2009

Keywords

  • cyclizations
  • imides
  • radical reactions
  • sulfur
  • tandem reactions
  • N-HETEROCYCLE SYNTHESIS
  • ALPHA-HALO AMIDES
  • GAMMA-LACTAMS
  • SUBSTITUTED PYRROLIDINONES
  • FUNCTIONAL REARRANGEMENT
  • CHAETOMELLIC ANHYDRIDE
  • CYCLIZATION REACTIONS
  • MILD CONDITIONS
  • CUCL-TMEDA
  • 5-ENDO

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