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Synthesis, Characterization, Crystal and Molecular Structure Analysis of 2,6-Dimethyl-3-Acetyl-5-Carbomethoxy-4-Phenyl-1,4-Dihydropyridine

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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 C17H19NO3 crystallizes in Monoclinic crystal class in space group P21/c with cell parameters a = 9.9130(12) Å, b = 7.3320(5) Å, c = 22.018(3) Å, β = 109.637(3)°, V = 1507.2(3) Å3 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–H···O and N–H···O. The pyridine ring gives boat conformation.

Graphical Abstract

The crystal and molecular structure of 2,6-dimethyl-3-acetyl-5-carbomethoxy-4-phenyl-1,4-dihydropyridine has been determined by X-ray diffraction methods.

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Acknowledgments

The authors are thankful for facility & grants given under University Grant Commission, New Delhi-Special Assistance Program; (DRS) Department Research Support (Sanction No. 540/6/DRS/2004, SAP-I, Dt. 26/03/2004), Department of Science and Technology, New Delhi Fund for Improvement of Science and Technology (FIST, sanction No. SR/FST/CSI-072/2003, Dt. 24/12/2003) and National facility for drug discovery through new chemical entities development and instrumentation support to small manufacturing pharma enterprises under DPRP project (Sanction No.VI-D&P/188/06-07/TDT, Dt. 30/03/07), Industries commissionerate, Government of Gujarat, Gandhinagar and also facility given by Department of Chemistry, Saurashtra University, Rajkot-360 005(INDIA) & to Amit Trivedi for UGC Meritorious fellowship by University Grant Commission, New Delhi.

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Authors and Affiliations

  1. Department of Chemistry, Saurashtra University, Rajkot, 360 005, India

    Amit Trivedi, Yogesh Naliapara & Anamik Shah

  2. Department of Physics, University of Mysore, Mysore, 570 006, India

    Neetha S. Gowda, M. A. Sridhar & J. Shashidhara Prasad

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  1. Amit Trivedi
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  2. Neetha S. Gowda
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  3. Yogesh Naliapara
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  4. M. A. Sridhar
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Correspondence to Anamik Shah.

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Trivedi, A., Gowda, N.S., Naliapara, Y. et al. Synthesis, Characterization, Crystal and Molecular Structure Analysis of 2,6-Dimethyl-3-Acetyl-5-Carbomethoxy-4-Phenyl-1,4-Dihydropyridine. J Chem Crystallogr 41, 774–778 (2011). https://doi.org/10.1007/s10870-010-9972-7

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