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 |
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Hauptverfasser: | , , , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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Zusammenfassung: | 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. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/jo0155198 |