title: Dihydropyridine-based multicomponent reactions. Efficient entry into new tetrahydroquinoline systems through Lewis acid-catalyzed formal [4 + 2] cycloadditions.
abstract: The three-component reaction of dihydropyridines, aldehydes, and p-methylaniline efficiently forms highly substituted tetrahydroquinolines in a stereoselective manner through a Lewis acid-catalyzed formal [4 + 2] cycloaddition. InCl(3) and Sc(OTf)(3) are the catalysts of choice for this process. The in situ generation of a reactive 1,4-dihydropyridine through the regioselective nucleophilic addition of cyanide to pyridinium salts allows a one-pot four-component transformation.
authors.affiliation: Parc Científic de Barcelona, University of Barcelona, Josep Samitier 1-5, 08028-Barcelona, Spain. rlavilla@pcb.ub.es
authors.forename: Rodolfo
authors.initials: R
authors.lastname: Lavilla
authors.forename: M Carmen
authors.initials: MC
authors.lastname: Bernabeu
authors.forename: Inés
authors.initials: I
authors.lastname: Carranco
authors.forename: José Luis
authors.initials: JL
authors.lastname: Díaz
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000814:Aniline Compounds / Q000737:chemistry; D003500:Cyclization; D004095:Dihydropyridines / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000814:Aniline Compounds; D004095:Dihydropyridines; D011804:Quinolines; C021313:methylaniline