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: Users 19 not found.
Date Deposited: 26 Aug 2019 05:18
Last Modified: 11 Jul 2022 07:08
URI: http://eprints.uni-mysore.ac.in/id/eprint/6999

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