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

Jean François Marcoux, Edward G. Corley, Kai Rossen, Phil Pye, Jimmy Wu, Michael A. Robbins, Ian W. Davies, Robert D. Larsen, Paul J. Reider

Research output: Contribution to journalArticle

44 Scopus citations

Abstract

(equation presented) α-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-withdrawmg groups at the β-position (R2). 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.

Original languageEnglish (US)
Pages (from-to)2339-2341
Number of pages3
JournalOrganic letters
Volume2
Issue number15
DOIs
StatePublished - Jul 27 2000
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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    Marcoux, J. F., Corley, E. G., Rossen, K., Pye, P., Wu, J., Robbins, M. A., Davies, I. W., Larsen, R. D., & Reider, P. J. (2000). Annulation of ketones with vinamidinium hexafluorophosphate salts: An efficient preparation of trisubstituted pyridines. Organic letters, 2(15), 2339-2341. https://doi.org/10.1021/ol006097b