Annulation of ketones with vinamidinium hexafluorophosphate salts: an efficient preparation of trisubstituted pyridines

Org Lett. 2000 Jul 27;2(15):2339-41. doi: 10.1021/ol006097b.

Abstract

alpha-Aryl ketones react with vinamidinium hexafluorophosphate salts to give access to the corresponding 3-arylpyridines. The annulation reactions proceed in good to excellent yields with vinamidinium salts containing electron-withdrawing groups at the beta-position (R(2)). The reaction was applied to the preparation of the COX-2 specific inhibitor 5-chloro-3-(4-methylsulfonyl)phenyl-2-(2-methyl-5-pyridinyl)pyridine (1), as well as a series of analogues.

MeSH terms

  • Cyclooxygenase Inhibitors / chemical synthesis*
  • Cyclooxygenase Inhibitors / chemistry
  • Cyclooxygenase Inhibitors / metabolism
  • Fluorides / chemistry*
  • Fluorides / metabolism
  • Ketones / chemistry*
  • Ketones / metabolism
  • Pyridines / chemical synthesis*
  • Pyridines / chemistry
  • Pyridines / metabolism

Substances

  • 5-chloro-3-(4-methylsulfonyl)phenyl-2-(2-methyl-5-pyridinyl)pyridine
  • Cyclooxygenase Inhibitors
  • Ketones
  • Pyridines
  • Fluorides