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Synthesis, characterization, crystal and molecular structure analysis of N-(2,4-dimethylphenyl)-6-methyl-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide

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Abstract

A novel dihydropyrimidine (DHPM) derivative bearing a carbamoyl moiety was synthesized by an efficient three-component Biginelli reaction and was characterized spectroscopically and finally confirmed by X-ray diffraction studies. The title compound C20H20N4O4 crystallizes in the monoclinic space group P21/c with cell parameters a=12.8970(12) Å, b=13.6210(11) Å, c=11.8420(13) Å, β=115.860(3)°, Z=4 and V=1872.0(3) Å3. The conformation of the dihydropyrimidine ring is unusual; it is planar instead of the usual boat-like conformation. The 3-nitrophenyl ring is orthogonal to the 3,4-DHPM ring. The carbonyl group is in an anti-clinal conformation.

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Notes

  1. CCDC 297693 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(0)1223-336033; e-mail: deposit@ccdc.cam.ac.uk).

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Acknowledgements

The authors would like to express their thanks to Department of Chemistry, Saurashtra University, Rajkot, for the laboratory facility and DST, Government of India, for financial assistance under the project SP/I2/FOO/93.

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Authors and Affiliations

  1. Department of Studies in Physics, Manasagangotri University of Mysore, Mysore, 570006, India

    S. Naveen, M. A. Sridhar & J. Shashidhara Prasad

  2. Department of Chemistry, Saurashtra University, Rajkot, 360005, India

    Priti Adlakha, Chintan Dholakia & Anamik Shah

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  1. S. Naveen
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Correspondence to M. A. Sridhar.

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Naveen, S., Adlakha, P., Dholakia, C. et al. Synthesis, characterization, crystal and molecular structure analysis of N-(2,4-dimethylphenyl)-6-methyl-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide. Struct Chem 17, 569–575 (2006). https://doi.org/10.1007/s11224-006-9073-6

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