A General Preparation of Pyridines and Pyridones via the Annulation of Ketones and Esters

A General Preparation of Pyridines and Pyridones via the Annulation of Ketones and Esters

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 hexa...

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Veröffentlicht in:Journal of organic chemistry 2001-06, Vol.66 (12), p.4194-4199
Hauptverfasser: Marcoux, Jean-François, Marcotte, Félix-Antoine, Wu, Jimmy, Dormer, Peter G, Davies, Ian W, Hughes, David, Reider, Paul J
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container_end_page 4199
container_issue 12
container_start_page 4194
container_title Journal of organic chemistry
container_volume 66
creator Marcoux, Jean-François
Marcotte, Félix-Antoine
Wu, Jimmy
Dormer, Peter G
Davies, Ian W
Hughes, David
Reider, Paul J
description 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.
doi_str_mv 10.1021/jo0155198
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title A General Preparation of Pyridines and Pyridones via the Annulation of Ketones and Esters
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