A general preparation of pyridines and pyridones via the annulation of ketones and esters |
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Authors: | Marcoux J F Marcotte F A Wu J Dormer P G Davies I W Hughes D Reider P J |
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Institution: | Department of Process Research, Merck & Co., Inc., P.O. Box 2000, Rahway, New Jersey 07065, USA. jeff_marcoux@merck.com |
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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 beta-position. The mechanism of the reaction was investigated by NMR and proceeds through the formation of a dienaminone intermediate. |
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