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Single Crystal X-ray Study of 6-Phenyl-4-(p-tolyl)pyridin-2(1H)-one

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Abstract

The title compound 6-phenyl-4-(p-tolyl)pyridin-2(1H)-one was synthesized via one-pot, three component reaction of (E)-1-phenyl-3-(p-tolyl)-2-propen-1-one, ethyl 2-nitroacetate and ammonium acetate in refluxing ethanol, as a shiny green crystalline solid in 83% yield. Its structure was characterized by spectral studies and unambiguously corroborated by X-ray diffraction crystallography. The crystals of title compound are monoclinic, sp. gr. P21/n, a = 11.8346(7) Å, b = 13.4413(9) Å, c = 17.7626(10) Å, β = 99.479(5)°, and Z = 8. All the rings in molecule of the title compound are planar. Hydrogen interactions play significant role in stabilizing the crystal structure and the supramolecular aggregate of molecules is facilitated by strong N–H···O and C–H···O type of hydrogen interactions.

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References

  1. S. S. P. Chou and P. W. Chen, Tetrahedron 64, 1879 (2008).

    Article  Google Scholar 

  2. S. D. Roughley and A. M. Jordan, J.Med. Chem. 54, 3451 (2011).

    Article  Google Scholar 

  3. L. A. Mitscher, Chem. Rev. 105, 559 (2005).

    Article  Google Scholar 

  4. B. Singh, E. R. Bacon, S. Robinson, et al., J. Med. Chem. 37, 248 (1994).

    Article  Google Scholar 

  5. V. Hagen, A. Rumler, G. Reck, et al., Pharmazie 44, 809 (1989).

    Google Scholar 

  6. M. J. Shiao, L. M. Shyn, and C. F. Chen, Heterocycles 31, 523 (1990).

    Article  Google Scholar 

  7. L. F. F. Abdel, Pharmazie 45, 283 (1990).

    Google Scholar 

  8. G. Wagner, H. Vieweg, and S. Leistner, Pharmazie 48, 576 (1993).

    Google Scholar 

  9. W. J. Coates and S. T. Flynn, CA 2027169 (1991).

    Google Scholar 

  10. I. M. A. Awad, A. E. Abdel-Rahman, and E. A. Bakhite, Phosphorus Sulfur Silicon Relat. Elem. 57, 293 (1991).

    Article  Google Scholar 

  11. A. U. Radushkin, I. F. Faermark, G. Y. Shvarts, and V. G. Granik, Khim. Farm. Zh. 26, 62 (1992).

    Google Scholar 

  12. G. E. H. Elgemeie, M. M. M. Sallam, S. M. Sherif, and M. H. Elnagdi, Heterocycle 23, 3107 (1985).

    Article  Google Scholar 

  13. M. E. Wall, M. C. Wani, C. E. Cook, et al., Am. Chem. Soc. 88, 3888 (1966).

    Article  Google Scholar 

  14. H. Josien and D. P. Curran, Tetrahedron 53, 8881 (1997).

    Article  Google Scholar 

  15. Z. Lv, C. Sheng, T. Wang, et al., J. Med. Chem. 53, 660 (2010).

    Article  Google Scholar 

  16. T. Harrison, C. R. Moyes, A. Nadin, et al., PCT WO98/50384.

  17. J. A. Spicer, G. W. Rewcastle, M. D. Kaufman, et al., J. Med. Chem. 50, 5090 (2007).

    Article  Google Scholar 

  18. E. Hu, A. Tasker, R. D. White, et al., Med. Chem. 51, 3065 (2008).

    Article  Google Scholar 

  19. R. Li, L. Xue, T. Zhu, et al., J. Med. Chem. 49, 1006 (2006).

    Article  Google Scholar 

  20. E. D. Thorsett and L. H. Latimer, Curr. Opin. Chem. Biol. 4, 377 (2000).

    Article  Google Scholar 

  21. R. Khajuria, P. Kannaboina, K. K. Kapoor, et al., Org. Biomol. Chem. 13, 5944 (2015).

    Article  Google Scholar 

  22. G. M. Sheldrick, Acta Crystallogr. A 64, 112 (2008).

    Article  ADS  Google Scholar 

  23. L. J. Farrugia, J. Appl. Crystallogr. 32, 837 (1999).

    Article  Google Scholar 

  24. M. Nardelli, J. Appl Crystallogr. 28, 659 (1995).

    Article  Google Scholar 

  25. A. L. Spek, Acta Crystallogr. D 65, 148 (2009).

    Article  Google Scholar 

  26. L. J. Farrugia, J Appl. Crystallogr. 30, 565 (1997).

    Article  Google Scholar 

  27. D. V. Albov, V. B. Rybakov, E. V. Babaev, and L. A. Aslanov, Crystallogr. Rep. 49, 430 (2004).

    Article  ADS  Google Scholar 

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Correspondence to Kamal K. Kapoor or Vivek K. Gupta.

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Khajuria, R., Sharma, S., Kapoor, K.K. et al. Single Crystal X-ray Study of 6-Phenyl-4-(p-tolyl)pyridin-2(1H)-one. Crystallogr. Rep. 62, 1144–1147 (2017). https://doi.org/10.1134/S1063774517070227

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  • DOI: https://doi.org/10.1134/S1063774517070227

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