Synthesis, Characterization, Crystal and Molecular Structure Analysis of 2,6-Dimethyl-3-acetyl-5-carbomethoxy-4-(3-nitrophenyl)-1,4-dihydropyridine

Autor: M. A. Sridhar, S. Naveen, Atul Manvar, S. Lakshmi, Anamik Shah, Priti Adlakha, Denish Karia, J. Shashidhara Prasad
Rok vydání: 2008
Předmět:
Zdroj: Journal of Chemical Crystallography. 39:389-394
ISSN: 1572-8854
1074-1542
DOI: 10.1007/s10870-008-9488-6
Popis: A novel unsymmetrical dihydropyridine, possessing carboxymethyl and carbomethoxy groups at C(3) and C(5), respectively, has been produced using a modified Hantzsch synthesis, under solvent free conditions, in a domestic microwave oven. The product obtained was characterized by spectroscopic techniques and finally confirmed by X-ray diffraction studies. The title compound C17H18N2O5 crystallizes in the monoclinic system in the space group P21/c with cell parameters a = 12.860(2) A, b = 7.4950(6) A, c = 16.734(3) A, β = 94.436(3)°, Z = 4 and V = 1608.1(4) A3. The 1,4-dihydropyridine ring in the structure is in a flattened boat conformation. The molecule possesses a chiral center at C4. The 3-nitrophenyl ring is nearly orthogonal to the 1,4-dihydropyridine ring. The carbonyl groups at C3 and C5 are oriented in −antiperiplanar and +synperiplanar conformations, respectively. The structure exhibits both inter and intramolecular hydrogen bonds of the type N–H···O and C–H···O. A novel unsymmetrical dihydropyridine, possessing carboxymethyl and carbomethoxy groups at C(3) and C(5) respectively, has been produced using a modified Hantzsch synthesis, under solvent free conditions, in a domestic microwave oven. The product obtained was characterized by spectroscipic techniques and finally confirmed by X-ray diffraction studies. The title compound C17H18N2O5 crystallizes in the monoclinic system in the space group P21/c with cell parameters a = 12.860(2) A, b = 7.4950(6) A, c = 16.734(3) A, β = 94.436(3)°, Z = 4 and V = 1608.1(4) A3. The 1,4-dihydropyridine ring in the structure is in a flattened boat conformation. The molecule possesses a chiral center at C(4). The 3-nitrophenyl ring is nearly orthogonal to the 1,4-dihydropyridine ring. The carbonyl groups at C(3) and C(5) are oriented in −antiperiplanar and +synperiplanar conformations respectively. The structure exhibits both inter and intramolecular hydrogen bonds of the type N–H···O and C–H···O.
Databáze: OpenAIRE
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