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One-Pot Synthesis of 1,4-Dihydropyridine Derivatives and Their X-Ray Crystal Structures: Role of Fluorine in Weak Interactions

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Abstract

1,4-dihydropyridines, namely diethyl 4-(4-fluorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (1a), diethyl 2,6-dimethyl-4-(3,4,5-trimethoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylate(1b), and diethyl 4-(3,4-dimethoxyphenyl)-2,6-dihydroxy-2,6-bis(trifluoromethyl)piperidine-3,5-dicarboxylate (2), are synthesized by one-pot multicomponent condensation of aromatic aldehyde with ethyl acetoacetate and liquid ammonia in the presence of an ethanol-water mixture and are characterized by single crystal X-ray diffraction. The effect of a fluorine atom on the dihydropyridine nucleus give insight into the self-assembly of compounds with various types of non-covalent interactions that greatly affect the crystal packing.

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References

  1. R. A. Janis, P. J. Silver, and D. J. Triggle. Adv. Drug Res., 1987, 16, 309.

    CAS  Google Scholar 

  2. F. Bossert and W. Vater. Med. Res. Rev., 1989, 9, 291.

    PubMed  CAS  Google Scholar 

  3. B. Loev, M. Goodman, K. Snader, R. Tedeschi, and E. Macko. J. Med. Chem., 1974, 17, 956.

    PubMed  CAS  Google Scholar 

  4. F. Bossert, H. Meyer, and E. Wehinger. Angew. Chem., Int. Ed., 1981, 20, 762.

    Google Scholar 

  5. V. M. Briukhanov, Ya. F. Zerev, and V. I. Elkin. Eksp. Klin. Farmakol., 1994, 57, 47.

    PubMed  CAS  Google Scholar 

  6. A. Hilgroth and H. Lilie. Eur. J. Med. Chem., 2003, 38, 495.

    Google Scholar 

  7. B. R. P. Kumar, P. Masih, E. Karthikeyan, A. Bansal, Suja, and P. Vijayan. Med. Chem. Res., 2010, 19, 344.

    Google Scholar 

  8. A. S. Kermani, H. Shafaroodi, R. Miri, H. Mirkhani, M. Vosooghi, and A. Shafiee. Med. Chem. Res., 2009, 18, 112.

    Google Scholar 

  9. G. A. Wachter, M. C. Davis, A. R. Martin, and S. G. Franzblau. J. Med. Chem., 1998, 41, 2436.

    PubMed  CAS  Google Scholar 

  10. K. Cooper, M. J. Fray, M. J. Parry, K. Richardson, and J. Steele. J. Med. Chem., 1992, 35, 3115.

    PubMed  CAS  Google Scholar 

  11. S.-J. Choi, J.-H. Cho, I. Im, S.-D. Lee, J.-Y. Jang, Y.-M. Oh, Y.-K. Jung, E.-S. Jeon, and Y.-C. Kim. Eur. J. Med. Chem., 2010, 45, 2578.

    CAS  Google Scholar 

  12. A. Davood, A. Nematollahi, M. Iman, and A. Shafiee. Arch. Pharmacal Res., 2009, 32, 481.

    CAS  Google Scholar 

  13. E. J. Roh, J. M. Keller, Z. Olah, M. J. Iadarola, and K. A. Jacobson. Bioorg. Med. Chem., 2008, 16, 9349.

    PubMed  PubMed Central  CAS  Google Scholar 

  14. K. Reichenbächer, H. I. Süss, and J. Hulliger. Chem. Soc. Rev., 2005, 34, 22–30.

    PubMed  Google Scholar 

  15. T. V. Rybakova and I. Yu. Bagryanskaya. J. Struct. Chem., 2009, 3(4), 741–753.

    Google Scholar 

  16. F. Babudri, G. M. Farinola, F. Naso, and R. Ragni. Chem. Commun., 2007, 1003.

  17. F. Leroux, P. Jeschke, and M. Schlosser. Chem. Rev., 2005, 105, 827.

    PubMed  CAS  Google Scholar 

  18. K. Sirisha, M. Chandra Shekar, K. Umasankar, P. Mahendar, A. Sadanandam, G. Achaiah, and V. Malla Reddy. Bioorg. Med. Chem., 2011, 19, 3249.

    PubMed  CAS  Google Scholar 

  19. A. Hantzsch. Justus Liebigs Ann. Chem., 1882, 215, 1.

    Google Scholar 

  20. A. S. Kotharkar and B. D. Shinde. Ukr. Bioorg. Acta, 2006, 1, 3.

    Google Scholar 

  21. S.-X. Wang, Z.-Y. Li, J.-C. Zhang, and J.-T. Li. Ultrason. Sonochem., 2008, 15, 677.

    PubMed  CAS  Google Scholar 

  22. J. Legeay, J. J. V. Eyndeb, and J. P. Bazureau. Tetrahedron, 2005, 61, 12386.

    CAS  Google Scholar 

  23. S. Deshayes, M. Liagre, A. Loupy, J. L. Luche, and A. Petit. Tetrahedron, 1999, 55, 10851.

    CAS  Google Scholar 

  24. W. H. Correa and J. L. Scott. Green Chem., 2001, 3, 296.

    CAS  Google Scholar 

  25. R. S. Varma. Green Chem., 1999, 1, 43.

    CAS  Google Scholar 

  26. S. D. Sharma, P. Hazarika, and D. Konwar. Catal. Commun., 2008, 9, 709.

    Google Scholar 

  27. M. Li, Z. Zuo, L. Wen, and S. Wang. J. Comb. Chem., 2008, 10, 436.

    PubMed  CAS  Google Scholar 

  28. Bruker. SMART, SAINT-Plus and SADABS. Madison, Wisconsin, Bruker AXS: USA, 1998.

    Google Scholar 

  29. G. M. Sheldrick. Acta Crystallogr., Sect. A, 2008, 64, 112.

    PubMed  CAS  Google Scholar 

  30. M. Nardelli. Acta Crystallogr., Sect. C, 1983, 39, 1141.

    Google Scholar 

  31. L. J. Farrugia. J. Appl. Crystallogr., 1997, 30, 565.

    CAS  Google Scholar 

  32. K. Brandenburg, H. Putz. DIAMOND. Crystal Impact GbR: Bonn, Germany, 2005.

    Google Scholar 

  33. D. O’Hagan. J. Org. Chem., 2012, 77, 3689–3699.

    PubMed  Google Scholar 

  34. V. H. Dalvi and P. J. Rossky. Proc. Natl. Acad. Sci. U. S. A., 2010, 107, 13603–13607.

    PubMed  PubMed Central  CAS  Google Scholar 

  35. P. Fenter. Langmuir, 1997, 7, 2013–2016.

    Google Scholar 

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Authors and Affiliations

  1. Department of Studies in Chemistry, Bangalore University, Bangalore, Karnataka, India

    R. Shashi, N. L. Prasad & N. S. Begum

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  1. R. Shashi
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  2. N. L. Prasad
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  3. N. S. Begum
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Correspondence to N. S. Begum.

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Additional Information

The CIF files have been deposited with the Cambridge Crystallographic Data Centre. The deposition number of compounds 1a, 1b, and 2 is CCDC-1889500, 1939480, and 1889485 respectively. These data can be obtained free of charge at www.ccdc.cam.ac.ul/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre (CCDC), 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(0)1223-336033; email: deposit@ccdc.cam.ac.uk.

Text © The Author(s), 2020, published in Zhurnal Strukturnoi Khimii, 2020, Vol. 61, No. 6, pp. 991–1000.

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Shashi, R., Prasad, N.L. & Begum, N.S. One-Pot Synthesis of 1,4-Dihydropyridine Derivatives and Their X-Ray Crystal Structures: Role of Fluorine in Weak Interactions. J Struct Chem 61, 938–947 (2020). https://doi.org/10.1134/S0022476620060141

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  • DOI: https://doi.org/10.1134/S0022476620060141

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