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The Use of 5-Hydroxymethylfurfural (5-HMF) in Multi-Component Hantzsch Dihydropyridine Synthesis
Jingjing Jiang1, Yves Queneau1, Florence Popowycz1
1INSA Lyon, Université Lyon 1, CNRS, CPE, UMR 5246, ICBMS, 1 rue Victor Grignard, F-69621, Villeurbanne Cedex.
This study explores using 5-hydroxymethylfurfural (5-HMF) in Hantzsch dihydropyridine synthesis via multi-component reactions. It efficiently produces symmetrical and unsymmetrical dihydropyridines from renewable 5-HMF.
Area of Science:
- Organic Chemistry
- Green Chemistry
- Sustainable Chemistry
Background:
- 5-hydroxymethylfurfural (5-HMF) is a renewable biobased platform chemical with broad applications.
- Limited research exists on the direct utilization of 5-HMF in fine chemistry, particularly in multi-component reactions (MCRs).
Purpose of the Study:
- To investigate the application of 5-HMF in the Hantzsch dihydropyridine synthesis.
- To develop efficient MCR protocols for synthesizing dihydropyridines derived from 5-HMF.
Main Methods:
- A three-component reaction strategy was employed using 5-HMF, aldehydes, and β-dicarbonyl compounds (β-ketoesters, 1,3-diketones).
- A four-component protocol was developed using β-ketoesters and dimedone with 5-HMF.
Main Results:
- The three-component reaction successfully synthesized symmetrical 1,4-dihydropyridines from 5-HMF in excellent yields.
- The four-component reaction efficiently produced unsymmetrical dihydropyridines.
Conclusions:
- 5-HMF can be effectively utilized in Hantzsch dihydropyridine synthesis through MCRs.
- This approach offers a sustainable route to valuable dihydropyridine derivatives from a renewable resource.
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