Three-component heterocyclization of gem-bromofluorocyclopropanes with NOBF4: access to 4-fluoropyrimidine N-oxides

J Org Chem. 2012 Nov 2;77(21):9893-9. doi: 10.1021/jo301880m. Epub 2012 Oct 25.

Abstract

Novel three-component heterocyclization involving gem-bromofluorocyclopropanes, nitrosyl tetrafluoroborate, and a molecule of the solvent (nitrile) yielding previously unknown fluorinated pyrimidine N-oxides is described. A two-step synthetic approach to 4-fluoropyrimidine N-oxides from alkenes under mild conditions is developed using this reaction. Mechanistic aspects of the heterocyclization are discussed.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkenes / chemistry
  • Cyclic N-Oxides
  • Cyclization
  • Cyclopropanes / chemistry*
  • Hydrocarbons, Halogenated / chemistry*
  • Molecular Structure
  • Nitriles / chemistry*
  • Solvents / chemistry

Substances

  • Alkenes
  • Cyclic N-Oxides
  • Cyclopropanes
  • Hydrocarbons, Halogenated
  • Nitriles
  • Solvents