From propargylamides to oxazole derivatives: NIS-mediated cyclization and further oxidation by dioxygen

J Org Chem. 2014 Apr 4;79(7):3052-9. doi: 10.1021/jo5001719. Epub 2014 Mar 19.

Abstract

NIS-mediated iodocyclization of N-sulfonyl propargylamides for the synthesis of various oxazolidines and iodoalkylidenedihydrooxazoles via a 5-exo-dig process is developed. The resulting iodoalkylidenedihydrooxazoles can be further transformed into the corresponding oxazoles in the presence of dioxygen.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Crystallography, X-Ray
  • Cyclization
  • Molecular Structure
  • Oxazoles / chemical synthesis*
  • Oxazoles / chemistry*
  • Oxidation-Reduction
  • Oxygen / chemistry*
  • Pargyline / analogs & derivatives*
  • Pargyline / chemistry*
  • Succinimides / chemistry*

Substances

  • Oxazoles
  • Succinimides
  • N-iodosuccinimide
  • Pargyline
  • Oxygen