Construction of a six-membered fused N-heterocyclic ring via a new 3-component reaction: synthesis of (pyrazolo)pyrimidines/pyridines

Chem Commun (Camb). 2012 Jan 11;48(3):431-3. doi: 10.1039/c1cc16418j. Epub 2011 Nov 10.

Abstract

A conceptually new three-component reaction was developed to construct a six-membered fused N-heterocyclic ring affording (pyrazolo)pyrimidines/pyridines as potential inhibitors of PDE4. The reaction is catalyzed by triflic acid in acetic acid in the presence of aerial oxygen.

MeSH terms

  • Binding Sites
  • Catalysis
  • Computer Simulation
  • Cyclic Nucleotide Phosphodiesterases, Type 4 / chemistry*
  • Cyclic Nucleotide Phosphodiesterases, Type 4 / metabolism
  • Heterocyclic Compounds / chemistry*
  • Mesylates / chemistry
  • Oxygen / chemistry
  • Phosphodiesterase 4 Inhibitors / chemical synthesis*
  • Phosphodiesterase 4 Inhibitors / chemistry
  • Phosphodiesterase 4 Inhibitors / pharmacology
  • Protein Structure, Tertiary
  • Pyrazoles / chemistry
  • Pyridines / chemical synthesis
  • Pyridines / chemistry*
  • Pyridines / pharmacology
  • Pyrimidines / chemical synthesis
  • Pyrimidines / chemistry*
  • Pyrimidines / pharmacology

Substances

  • Heterocyclic Compounds
  • Mesylates
  • Phosphodiesterase 4 Inhibitors
  • Pyrazoles
  • Pyridines
  • Pyrimidines
  • Cyclic Nucleotide Phosphodiesterases, Type 4
  • trifluoromethanesulfonic acid
  • pyrimidine
  • pyridine
  • Oxygen