One-Pot Metal-Free Synthesis of 3-CF3-1,3-Oxazinopyridines by Reaction of Pyridines with CF3CO-Acetylenes

Molecules. 2019 Oct 6;24(19):3594. doi: 10.3390/molecules24193594.

Abstract

The reaction of pyridines with trifluoroacetylated acetylenes was investigated. It was found that the reaction of various pyridines with two molecules of CF3CO-acetylenes proceeds under mild metal-free conditions. As a result, efficient stereoselective synthesis of 3-arylethynyl-3-trifluoromethyl-1,3-oxazinopyridines was elaborated. Target heterocycles can be prepared in up to quantitative yields.

Keywords: 1,3-oxazines; CF3CO-acetylenes; fluorinated heterocycles; pyridine.

MeSH terms

  • Alkynes / chemistry*
  • Halogenation
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Molecular Structure
  • Pyridines / chemistry*

Substances

  • Alkynes
  • Heterocyclic Compounds
  • Pyridines