Bradley University, Mund-Lagowski Department of Chemistry and Biochemistry, Peoria, IL 61606
An alternative method for the synthesis of amides has been discovered. By reacting a beta-ketoester monoanion with 1 or 2 equivalents of a primary or secondary amine, an amide is generated. Because both carbonyls of the beta-ketoester undergo amidation,the only side product from the reaction is ethanol when 2 equivalents of an amine are used.Previous work in amide synthesis from beta-ketoesters hasshown that an electron-withdrawing group on the alpha-carbon is necessary for stabilization of the leaving group. Our work focused on identifying the general reaction conditions for the production of a variety of amides and on determination of mechanism by which the reaction occurs.
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