Synthesis, characterization, crystal and molecular structure analysis of 2,6-dimethyl-3-acetyl-5-carbomethoxy-4-(3-nitrophenyl)-1,4-dihydropyridi ne

Adlakha, Priti and Naveen, S. and Lakshmi, S. and Manvar, Atul and Karia, Denish and Anamik Shah and Sridhar, M. A. and Shashidhara Prasad, J. (2009) Synthesis, characterization, crystal and molecular structure analysis of 2,6-dimethyl-3-acetyl-5-carbomethoxy-4-(3-nitrophenyl)-1,4-dihydropyridi ne. Journal of Chemical Crystallography, 39 (6). pp. 389-394. ISSN 1572-8854

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Official URL: http://doi.org/10.1007/s10870-008-9488-6

Abstract

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 P2(1)/c with cell parameters a = 12.860(2) angstrom, b = 7.4950(6) angstrom, c = 16.734(3) angstrom, beta = 94.436(3)degrees, Z = 4 and V = 1608.1(4) angstrom(3). 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 center dot center dot center dot O and C-H center dot center dot center dot O.

Item Type: Article
Uncontrolled Keywords: 1,4-Dihydropyridine; Hantzsch synthesis; Crystal structure; Flattened boat; Hydrogen bonds
Subjects: D Physical Science > Physics
Divisions: Department of > Physics
Depositing User: Shrirekha N
Date Deposited: 26 Aug 2019 05:18
Last Modified: 26 Aug 2019 05:18
URI: http://eprints.uni-mysore.ac.in/id/eprint/6999

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