An annulation method for the synthesis of alkyl-substituted 6-carbomethoxy-2-pyridones |
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Authors: | Yu Zhang |
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Institution: | Department of Chemistry and Biochemistry, Brigham Young University, Provo, UT 84602, United States |
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Abstract: | A protocol for the synthesis of 5-alkyl and 3,5-dialkyl-6-carbomethoxy-2-pyridones was devised. Key steps include a Mannich reaction, acylation of a tosylamine, and a PPh3/TiCl4-promoted intramolecular Reformatsky-type reaction with a thioester as the electrophile. The latter process typically afforded a vinylogous thiocarbamate via elimination of water rather than the Dieckmann-type product which would have resulted from elimination of the thiol. However, the Dieckmann-type ketone product was obtained in one instance. Subsequent elimination of the tosyl group and desulfurization completed the pyridone synthesis. |
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Keywords: | Lyconadin A Pyridone Mannich reaction Reformatsky reaction Desulfurization |
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