1‐Alkyl(aryl)quinolinium chlorides are oxidized by rabbit liver aldehyde oxidase at positions C‐2 and C‐4. The site and the maximum rate of oxidation are dependent on the size and the steric conformation of the N‐1 substituent. The presence of a 3‐carboxamido group directs the oxidation completely to position C‐4, irrespective of the size of the N‐substituent. Application of covalent amination in liquid ammonia as an “enzyme model” for the oxidation of these compounds shows little resemblance.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.