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 C 17 H 19 NO 3 crystallizes in Monoclinic crystal class in space group P2 1 /c with cell parameters a = 9.9130(12) Å , b = 7.3320(5) Å , c = 22.018(3) Å , b = 109.637(3)°, V = 1507.2(3) Å 3 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-HÁÁÁO and N-HÁÁÁO. The pyridine ring gives boat conformation.

Structure and Antibacterial Activity of 3-(3,4-Dimethoxyphenyl)furan-2(5H)-ones

“…The center five-member ring is therefore identified as a furan-2(5H)-one, which are consistent with the analogues previously reported [11,12]. An sp 3 orbital of O2, O3, O4 or O5 is conjugated with the attached double bond, which shortens the bond length of C-O from about 1.43 Å [15,16] to 1.36 Å . O3-C10 (1.333(2) Å ) is further shortened by the strong electron withdrawing effect of carbonyl group (C8-O1), which is intermediated by p molecular orbital of C7-C10.…”