Synthesis of Dichlorophenyl-, Cyanophenyl- and Quinolinyl-Substituted alpha-Ethoxyacetic Acids and Derivatives, via alpha-Hydroxyarylacetic Acids

A synthetic approach to novel series of alpha-ethoxy-alpha-phenylacetamides and alpha-ethoxy-alpha-quinolinylacetamides was developed. Aryl aldehydes were converted to cyanohydrins, which were then hydrolyzed or alcoholyzed. Following ethylation of the alpha-hydroxy group, peptide-coupling protocols were used to produce the target amides. These amides, together with the alpha-ethoxy intermediates, have significant potential for a broad range of application including as antimalarial, fungicidal, bactericidal, anticoagulant, hypolipidemic and sleep-promoting agents.