Catalysis by basic carbons: Preparation of dihydropyridines

Abstract

The condensation of benzaldehyde and different substituted benzaldehydes, such as 2-nitrobenzaldehyde, 3-nitrobenzaldehyde, and 2,4-dichlorobenzaldehyde, with ethyl cyanoacetate was carried out using two alkaline carbons (Na-Norit and Cs-Norit) as catalysts in the absence of solvent. The reaction products are precursors in the production of 1,4-dihydropyridine derivatives, which have expanding practical applications as pharmaceuticals in the line of calcium channel blockers. High values of activity and selectivity were obtained. The most active carbon (Cs-Norit), which contains basic sites with p K b = 11.2, is more active than pyridine, and less than piperidine. The selectivity to the desired condensation product when using these activated carbons is, at least, as high as in the case of the homogeneous catalyst. This “green” and “clean” method (alkaline doped carbon catalyst in the absence of solvent) can be extended to the preparation of other intermediates with medical applications.