Synthesis,Characterization, Crystal and Molecular Structure Analysis of 2,6-Dimethyl-3-acetyl-5-carbomethoxy-4-(3-nitrophenyl)-1,4-dihydropyridine |
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Authors: | Priti Adlakha S Naveen S Lakshmi Atul Manvar Denish Karia Anamik Shah M A Sridhar J Shashidhara Prasad |
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Institution: | (1) Department of Chemistry, Saurashtra University, Rajkot, 360 005, India;(2) Department of Studies in Physics, Manasagangotri University of Mysore, Mysore, 570 006, India |
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Abstract: | 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 P21/c with cell parameters a = 12.860(2) ?, b = 7.4950(6) ?, c = 16.734(3) ?, β = 94.436(3)°, Z = 4 and V = 1608.1(4) ?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···O and
C–H···O.
Index 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 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) ?, b = 7.4950(6) ?, c = 16.734(3) ?, β = 94.436(3)°, Z = 4 and V = 1608.1(4) ?3. 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.
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Keywords: | 1 4-Dihydropyridine Hantzsch synthesis Crystal structure Flattened boat Hydrogen bonds |
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