Dihydropyridines in MCRs. Tandem processes leading to modular tetrahydroquinoline systems with up to 6 diversity elements.
An efficient, modular method for the synthesis of highly substituted tetrahydroquinoline systems is described. The Lewis acid catalyzed interaction of dihydropyridines with glyoxalate and anilines affords the heterocyclic parent systems in good yields. Tandem one-pot processes allow the incorporation of additional components: a preliminary nucleophilic attack on pyridinium salts generates the reactive dihydropyridine in situ, and subsequent electrophilic reactions on the secondary amine complete the assembly of the final targets, which have up to 6 diversity points.
Lavilla
Rodolfo
R
Parc Científic de Barcelona, Josep Samitier, 1-5, 08028 Barcelona, Spain. rlavilla@pcb.ub.es
Carranco
Inés
I
Díaz
José Luis
JL
Bernabeu
M Carmen
MC
de la Rosa
Guillermo
G
D000447:Aldehydes / Q000737:chemistry; D000814:Aniline Compounds / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D004095:Dihydropyridines / Q000737:chemistry*; D006038:Glyoxylates / Q000737:chemistry; D015394:Molecular Structure
D000447:Aldehydes; D000814:Aniline Compounds; D004095:Dihydropyridines; D006038:Glyoxylates; C031150:glyoxylic acid