The Rügheimer-Burrows reaction revisited: Facile preparation of 4-alkylisoquinolines and 3,5-dialkylpyridines from (partially) saturated amines.

A long-known class of cyclic amine/aldehyde condensation reactions was reinvestigated. Benzoic acid was found to efficiently promote condensations of amines such as piperidine or 1,2,3,4-tetrahydroisoquinoline with aromatic aldehydes, resulting in amine β-functionalization and aromatization. These redox-neutral transformations provide 3,5-dialkylpyridines and 4-alkylisoquinolines in moderate to good yields, following short reaction times under microwave conditions.