ORGN 511 |
| Treatment of thioaroylketene S,N-acetals 1 with in situ generated (chloro)phenylketenes 4a or chloroketenes 4b in CH2Cl2 at –78oC, followed by warming to room temperature gave 2-(1H)-pyridone derivatives 3 in moderate to excellent yields. On heating 1-methyl-6-methylsulfanyl-3,4-diphenyl-2-(1H)-pyridone 3a in the presence of m-CPBA (3 equiv.) in CHCl3 for 5 h, 6-methanesulfonyl-1-methyl-3,4-diphenyl-2-(1H)-pyridones 10. Reactions of 10 with various types of nucleophiles, especially carbon nucleophiles, afforded 6-substituted compounds 13. Subsequent treatment of 6-{2-(2-aminophenyl)-2-oxo-ethyl}-1-methyl-3,4-diphenyl-2-(1H)-pyridones 13d with ethylene glycol (20 equiv.) in the presence of TsOH in toluene at reflux for 16 h gave 6-(2-hydroxy-ethoxy)-2,3-diphenyl-pyrido[1,2-a]quinolin-1-ones 15.
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Heterocycles, Aromatics, Metal-Mediated Reactions and Syntheses, Materials, Devices, and Switches
8:00 PM-10:00 PM, Wednesday, 29 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster
Division of Organic Chemistry |
