Issue 23, 2009

l-Proline-catalyzed synthesis of highly functionalized multisubstituted 1,4-dihydropyridines

Abstract

Highly functionalized multisubstituted 1,4-dihydropyridines 5 have been concisely synthesized in moderate to good yields viaL-proline-catalyzed one-pot multicomponent reactions (MCRs) of alkynoates or alkynones 1, amines 2, β-dicarbonyl compounds 3 and aldehydes 4 under mild conditions. The MCR process involves hydroamination/Knoevenagel condensation/Michael-type addition/intramolecular cyclization processes and leads to the formation of 1,4-dihydropyridines 5. The molecular structure of 5ckaa was confirmed by single-crystal X-ray diffraction. This method is energy saving and environmentally friendly, providing easy access to diverse multisubstituted polyfunctional 1,4-dihydropyridines.

Graphical abstract: l-Proline-catalyzed synthesis of highly functionalized multisubstituted 1,4-dihydropyridines

Supplementary files

Article information

Article type
Paper
Submitted
20 Jul 2009
Accepted
08 Sep 2009
First published
05 Oct 2009

Org. Biomol. Chem., 2009,7, 4943-4953

L-Proline-catalyzed synthesis of highly functionalized multisubstituted 1,4-dihydropyridines

H. Jiang, R. Mai, H. Cao, Q. Zhu and X. Liu, Org. Biomol. Chem., 2009, 7, 4943 DOI: 10.1039/B914659H

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