| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5222812 | Tetrahedron | 2009 | 7 Pages |
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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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Yu Zhang, Brad M. Loertscher, Steven L. Castle,