title: The Rügheimer-Burrows reaction revisited: Facile preparation of 4-alkylisoquinolines and 3,5-dialkylpyridines from (partially) saturated amines.
abstract: 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.
authors.affiliation: Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, United States ; Department of Organic Synthesis Technology, Ural Federal University, Yekaterinburg, 620002, Russia.
authors.forename: Alena Yu
authors.initials: AY
authors.lastname: Platonova
authors.affiliation: Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, United States.
authors.forename: Daniel
authors.initials: D
authors.lastname: Seidel
keywords: azomethine ylides; heterocycles; redox-neutral