Dihydropyridine-based multicomponent reactions. Efficient entry into new tetrahydroquinoline systems through Lewis acid-catalyzed formal [4 + 2] cycloadditions.
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.
Lavilla
Rodolfo
R
Parc Científic de Barcelona, University of Barcelona, Josep Samitier 1-5, 08028-Barcelona, Spain. rlavilla@pcb.ub.es
Bernabeu
M Carmen
MC
Carranco
Inés
I
Díaz
José Luis
JL
D000447:Aldehydes / Q000737:chemistry; D000814:Aniline Compounds / Q000737:chemistry; D003500:Cyclization; D004095:Dihydropyridines / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000447:Aldehydes; D000814:Aniline Compounds; D004095:Dihydropyridines; D011804:Quinolines; C021313:methylaniline