N-Methoxy-N-methyl-3-bromopropionamide: a new three carbon homologating agent for the synthesis of unsymmetrical 1,4-diketones

A synthetic route based on a three carbon homologation of an α-aminonitrile was developed for the synthesis of unsymmetrical 1,4-diketones. The key steps were the alkylation of various aryl and heteroaryl α-aminonitriles with N-methoxy-N-methyl-3-bromopropionamide followed by the addition of a Grignard reagent to the alkylated product and then subsequent hydrolysis.