Annulation of Ketones with Vinamidinium Hexafluorophosphate Salts:  An Efficient Preparation of Trisubstituted Pyridines

α-Aryl ketones react with vinamidinium hexafluorophosphate salts to give access to the corresponding 3-arylpyridines. The annulation reactions proceed in good to excellent yields with vinamidinium salts containing electron-withdrawing groups at the β-position (R2). The reaction was applied to the pr...

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Veröffentlicht in:Organic letters 2000-07, Vol.2 (15), p.2339-2341
Hauptverfasser: Marcoux, Jean-François, Corley, Edward G, Rossen, Kai, Pye, Phil, Wu, Jimmy, Robbins, Michael A, Davies, Ian W, Larsen, Robert D, Reider, Paul J
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Sprache:eng
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Zusammenfassung:α-Aryl ketones react with vinamidinium hexafluorophosphate salts to give access to the corresponding 3-arylpyridines. The annulation reactions proceed in good to excellent yields with vinamidinium salts containing electron-withdrawing groups at the β-position (R2). The reaction was applied to the preparation of the COX-2 specific inhibitor 5-chloro-3-(4-methylsulfonyl)phenyl-2-(2-methyl-5-pyridinyl)pyridine (1), as well as a series of analogues.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol006097b