Synthesis, Characterization, Crystal and Molecular Structure Analysis of 2,6-Dimethyl-3-Acetyl-5-Carbomethoxy-4-Phenyl-1,4-Dihydropyridine

Abstract

The synthesis of a novel unsymmetrical dihydropyridine, bearing carboxy methyl and carbomethoxy groups at C(3) and C(5), respectively, has been achieved by applying the modified Hantzsch-type condensation, which involves the Michael addition of Knoevenagel adduct with an enamine. The product obtained was characterized by spectroscopic techniques and finally confirmed by X-ray diffraction studies. The title compound C17H19NO3 crystallizes in Monoclinic crystal class in space group P21/c with cell parameters a = 9.9130(12) Å, b = 7.3320(5) Å, c = 22.018(3) Å, β = 109.637(3)°, V = 1507.2(3) Å3 and Z = 4. The final residual factor R 1 = 0.0642. The structure exhibits both intra and inter-molecular hydrogen bonding of the type C–H···O and N–H···O. The pyridine ring gives boat conformation. The crystal and molecular structure of 2,6-dimethyl-3-acetyl-5-carbomethoxy-4-phenyl-1,4-dihydropyridine has been determined by X-ray diffraction methods.