One-Pot Multicomponent Reactions for the Efficient Synthesis of Highly Functionalized Dihydropyridines

Abstract

An efficient, atom-economic, one-pot protocol has been developed for the synthesis of highly functionalized dihydropyridines via four-component reactions of aromatic aldehydes, arylamines, malononitrile, and dimethylacetylenedicarboxylate in the presence of sodium hydroxide in ethanol. This domino reaction proceeded smoothly in good to excellent yields and offered several advantages, including short reaction time, simple experimental procedure, and applicability to a broad range of substrates.

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GRAPHICAL ABSTRACT

Keywords:

• Aldehydes
• amines
• dihydropyridines
• dimethylacetylenedicarboxylate
• multicomponent reactions

ACKNOWLEDGMENTS

L. H. C. and T. P. gratefully acknowledge financial support from the Department of Science and Technology India, with Sanction No. SR/FT/CS-042/2009 and SR/FT/CS-008/2010 respectively. S. P. is thankful to the University Grants Commission for his junior research fellowship. Authors are also grateful to SAIF, CDRI Lucknow and SAIF, Indian Institute of Technology Madras, for providing NMR facilities for characterization of the compounds.

Notes

^a All the reactions were carried out using 4-chlorobenzaldehyde, 4-methylaniline, malononitrile, and dimethylacetylenedicarboxylate in 1:1:1:1 ratio.

^b Isolated yield.

^a Isolated yields.

^b Literature reference.