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

Authors
Marcoux, JF Marcotte, FA Wu, J Dormer, PG Davies, IW Hughes, D Reider, PJ
Citation
Jf. Marcoux et al., A general preparation of pyridines and pyridones via the annulation of ketones and esters, J ORG CHEM, 66(12), 2001, pp. 4194-4199
Citations number
35
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
66
Issue
12
Year of publication
2001
Pages
4194 - 4199
Database
ISI
SICI code
0022-3263(20010615)66:12<4194:AGPOPA>2.0.ZU;2-W
Abstract
A general preparation of pyridines 4a-f from stabilized ketones 3a-c and ar yl ketones 3d-f is described. The annulation of stabilized esters 3g,h give s access to the corresponding 2-pyridones 4g,h. The annulation reactions pr oceed in fair to excellent yields (46-87%) with vinamidinium hexafluorophos phate salts 2a-d containing electron-withdrawing groups at the beta -positi sn. The mechanism of the reaction was investigated by NMR and proceeds thro ugh the formation of a dienaminone intermediate.