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 incorporatio...

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Bibliographic Details
Published in:Molecular diversity 2003, Vol.6 (3-4), p.171-175
Main Authors: Lavilla, Rodolfo, Carranco, Inés, Díaz, José Luis, Bernabeu, M Carmen, de la Rosa, Guillermo
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Amino acids
Aniline Compounds - chemistry
Biophysics
Biosynthesis
Combinatorial Chemistry Techniques
Cyclization
Dihydropyridines - chemistry
Glyoxylates - chemistry
Molecular biology
Molecular Structure
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Summary: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.
ISSN:1381-1991
1573-501X
DOI:10.1023/B:MODI.0000006756.83821.80