Synthesis of substituted quinolines from 1-acetyladamantane

1-Acetyladamantane reacts with phosphorus pentachloride and dimethylformami de to give 3-(1-adamantyl)-3-chloro-2-propenal whose reactions with primary aromatic amines result in formation of N-(1-adamantyl-3-arylimino-1-propen yl)aniline hydrochlorides. The latter undergo intramolecular cyclization to 6- and 7-substituted 2-(1-adamantyl)quinolines on heating in boiling glaci al acetic acid.