A general preparation of pyridines and pyridones via the annulation of ketones and esters

J. F. Marcoux, F. A. Marcotte, J. Wu, P. G. Dormer, I. W. Davies, D. Hughes, P. J. Reider

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Abstract

A general preparation of pyridines 4a-f from stabilized ketones 3a-c and aryl ketones 3d-f is described. The annulation of stabilized esters 3g,h gives access to the corresponding 2-pyridones 4g,h. The annulation reactions proceed in fair to excellent yields (46-87%) with vinamidinium hexafluorophosphate salts 2a-d containing electron-withdrawing groups at the β-position. The mechanism of the reaction was investigated by NMR and proceeds through the formation of a dienaminone intermediate.

Original languageEnglish (US)
Pages (from-to)4194-4199
Number of pages6
JournalJournal of Organic Chemistry
Volume66
Issue number12
DOIs
StatePublished - Jun 15 2001
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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    Marcoux, J. F., Marcotte, F. A., Wu, J., Dormer, P. G., Davies, I. W., Hughes, D., & Reider, P. J. (2001). A general preparation of pyridines and pyridones via the annulation of ketones and esters. Journal of Organic Chemistry, 66(12), 4194-4199. https://doi.org/10.1021/jo0155198