Skip to main content
SpringerLink
Log in

Synthesis and structure of regioisomeric amino enones containing 2-pyridyl and CF3 substituents

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Regioisomeric amino enones (Z)-4-amino-1,1,1-trifluoro-4-(2-pyridyl)but-3-en-2-one and (Z)-3-amino-4,4,4-trifluoro-1-(2-pyridyl)but-2-en-1-one were synthesized by the reaction of lithium (Z)-1,1,1-trifluoro-4-oxo-4-(2-pyridyl)but-2-en-2-olate with ammonium acetate in glacial AcOH. A comparative study of physicochemical properties and the crystal structures showed that the molecules of these new compounds are planar (except for two fluorine atoms) with an U-shaped configuration of the keto enamine moiety. A change in the position of the amino group with respect to the CF3 substituent leads to significant changes in the electron density distribution and the C-C bond lengths in the keto enamine moiety and also in the character of intermolecular hydrogen bonds responsible for the crystal packing mode of regioisomeric amino enones.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. S. Kovács, Z. Novák, Tetrahedron, 2013, 69, 8987; DOI: https://doi.org/10.1016/j.tet.2013.08.047.

    Article  CAS  Google Scholar 

  2. I. O. Edafiogho, S. B. Kombian, K. V. V. Ananthalakshmi, N. N. Salama, N. D. Eddington, T. L. Wilson, M. S. Alexander, P. L. Jackson, C. D. Hanson, J. Pharm. Sci., 2007, 96, 2509; DOI:https://doi.org/10.1002/jps.20967.

    Article  CAS  PubMed  Google Scholar 

  3. N. D. Eddington, Curr. Med. Chem., 2000, 7, 417; DOI: https://doi.org/10.1515/ncrs-2015-0121.

    Article  CAS  PubMed  Google Scholar 

  4. N. N. Salama, N. D. Eddington, D. Payne, T. L. Wilson, K. R. Scott, Curr. Med. Chem., 2004, 11, 2093; DOI:https://doi.org/10.2174/0929867043364766.

    Article  CAS  PubMed  Google Scholar 

  5. I. O. Edafiogho, C. N. Hinko, H. Chang, J. A. Moore, D. Mulzac, J. M. Nicholson, K. R. Scott, J. Med. Chem., 1992, 35, 2798; DOI:https://doi.org/10.1021/jm00093a012.

    Article  CAS  PubMed  Google Scholar 

  6. S. B. Kombian, I. O. Edafiogho, K. V. V. Ananthalakshmi, Br. J. Pharmacol., 2005, 145(7), 945; DOI: https://doi.org/10.1038/sj.bjp.0706250.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. K. R. Scott, I. O. Edafiogho, E. L. Richardson, V. A. Farrar, J._A. Moore, E. l. Tietz, C. N. Hinko, H. Chang, A. El-Assadi, J. M. Nicholson, J. Med. Chem., 1993, 36, 1947.

    Article  CAS  PubMed  Google Scholar 

  8. K. R. Scott, G. O. Rankin, J. P. Stables, M. S. Alexander, I. O. Edafiogho, V. A. Farrar, K. R. Kolen, J. A. Moore, L. D. Sims, A. D. Tonnu, J. Med. Chem., 1995, 38, 4033.

    Article  CAS  PubMed  Google Scholar 

  9. F. Fenain, M. Me’debielle, M. Rocher, O. Onomura, E. Okada, D. Shibata. J. Fluor. Chem., 2007, 128, 1286; DOI: https://doi.org/10.1016/j.jfluchem.2007.06.001.

    Article  CAS  Google Scholar 

  10. V. N. Charushin, N. N. Mochulskaya, A. A. Andreiko, V. I. Filyakova, M. I. Kodess, O. N. Chupakhin, Tetrahedron Lett., 2003, 44, 2421; DOI: https://doi.org/10.1016/S0040-4039(03)00060-1.

    Article  CAS  Google Scholar 

  11. V. I. Filyakova, V. G. Ratner, N. S. Karpenko, K. I. Pashkevich, in Enaminy v organicheskom sinteze [Enamines in Organic Synthesis], Sverdlovsk, 1996, 29 (in Russian).

  12. Y. A. Davydova, T. M. Sokolenko, Y. L. Yagupolskii, J. Fluor. Chem., 2014, 157, 58; DOI: https://doi.org/10.1016/j.jfluchem.2013.11.007.

    Article  CAS  Google Scholar 

  13. S. Doherty, R. J. Errington, N. Housley, J. Ridland, W. Clegg, M. R. J. Elsegood, Organometallics, 1999, 18, 1018; DOI: https://doi.org/10.1021/om980510q.

    Article  CAS  Google Scholar 

  14. J. Kim, J.W. Hwang, Y. Kim, M. H. Lee, Y. Han, Y. Do, J. Organomet. Chem., 2001, 620, 1; DOI: https://doi.org/10.1016/S0022-328X(00)00555-6.

    Article  CAS  Google Scholar 

  15. Yu. S. Varshavskii, T. G. Cherkasova, K. I. Pashkevich, V. I. Filyakova, L. V. Osetrova, N. A. Buzina, Koord. Khim., 1992, 18, 188 [Russ. J. Coord. Chem. (Engl. Transl.), 1992, 18].

    CAS  Google Scholar 

  16. V. I. Filyakova, D. L. Chizhov, E. F. Khmara, V. N. Charushin, Russ. J. Gen. Chem., 2010, 80, 190; DOI: https://doi.org/10.1134/S1070363210010317.

    Article  CAS  Google Scholar 

  17. D. L. Chizhov, M. G. Pervova, M. A. Samorukova, E. F. Khmara, V. I. Filyakova, V. I. Saloutin, V. N. Charushin, J. Fluor. Chem., 2011, 132, 394; DOI: https://doi.org/10.1016/j.jfluchem.2011.03.018.

    Article  CAS  Google Scholar 

  18. N. Chopin, G. Novitchi, M. Médebielle, G. Pilet, J. Fluorine Chem., 2015, 179, 169; DOI: https://doi.org/10.1016/j.jfluchem.2015.06.023.

    Article  CAS  Google Scholar 

  19. N. Chopin, M. Médebielle, O. Maury, G. Novitchi, G. Pilet, Eur. J. Inorg. Chem., 2014, 6185; DOI: https://doi.org/10.1002/ejic.201402714.

  20. N. Chopin, G. Pilet, Y. Morita, M. Médebielle, J. Fluor. Chem., 2014, 67, 211; DOI: https://doi.org/10.1016/j.jfluchem.2014.07.005.

    Article  CAS  Google Scholar 

  21. V. I. Filyakova, V. G. Ratner, N. S. Karpenko, K. I. Pashkevich, Russ. Chem. Bull., 1996, 45, 2163; DOI: https://doi.org/10.1007/BF01430731.

    Article  Google Scholar 

  22. N. S. Karpenko, V. I. Filyakova, K. I. Pashkevich, Russ. J. Org. Chem., 1997, 33, 1724; DOI: https://doi.org/10.1002/chin.199835087.

    Google Scholar 

  23. N. S. Boltachova, O. V. Fedorova, I. G. Ovchinnikova, O. N. Kazheva, A. N. Chekhlov, O. A. Dyachenko, G. L. Rusinov, V. I. Filyakova, V. N. Charushin, J. Fluor. Chem., 2007, 128, 762; DOI: https://doi.org/10.1016/j.jfluchem.2007.04.017.

    Article  CAS  Google Scholar 

  24. E. F. Zhilina, P. A. Slepukhin, N. S. Boltacheva, M. G. Pervova, D. L. Chizhov, V. I. Filyakova, V. N. Charushin, Russ. J. Gen. Chem., 2012, 82, 1962; DOI: https://doi.org/10.1134/S1070363212120092.

    Article  CAS  Google Scholar 

  25. N. S. Boltacheva, V. I. Filyakova, V. N. Charushin, Russ. J. Org. Chem., 2005, 41, 1452; DOI: https://doi.org/10.1007/s11172-010-0314-x.

    Article  CAS  Google Scholar 

  26. R. Cea-Olivares, I. Rodriguez, M. J. Rosales, A. Toscano, Aust. J. Chem., 1984, 37, 879.

    Article  CAS  Google Scholar 

  27. D. A. Johnson, A. B. Waugh, T. W. Hambley, J. C. Taylor, J. Fluor. Chem., 1985, 27, 371; DOI:https://doi.org/10.1016/S0022-1139(00)80908-2.

    Article  CAS  Google Scholar 

  28. V. I. Filyakova, D. S. Yufit, Y. T. Struchkov, K. I. Pashkevich, Bull. Acad. Sci. USSR. Div. Chem. Sci., 1990, 39, 936; DOI: https://doi.org/10.1007/BF00961686.

    Article  Google Scholar 

  29. J. Przyborowski, E. Lork, G.-V. Röschenthaller, J. Fluor. Chem., 2000, 104, 207; DOI: https://doi.org/10.1016/S0022-1139(00)00245-1.

    Article  CAS  Google Scholar 

  30. G. I. Zharkova, I. A. Baidina, A. I. Smolentsev, P. A. Stabnikov, N. B. Morozova, J. Struct. Chem., 2017, 58, 970; DOI: https://doi.org/10.1134/S002247661705016X.

    Article  CAS  Google Scholar 

  31. J.-L. Wang, F. Ding, M. Yu, F.-M. Miao, Jiegou Huaxue (Chin. J. Struct. Chem.), 2004, 1, 41.

    Google Scholar 

  32. M. Rocha, D. M. Gil, G. A. Echeverría, O. E. Piro, J. L. Jios, S. E. Ulice, J. Fluor. Chem., 2018, 208, 36; DOI: https://doi.org/10.1016/j.jfluchem.2018.01.001.

    Article  CAS  Google Scholar 

  33. A. Hidalgo, L. P. Avendaño Jiménez, L. A. Ramos, M. A. Mroginski, J. L. Jios, S. E. Ulic, G. A. Echeverría, O. E. Piro, E. Castellano, J. Phys. Chem., A, 2012, 116, 1110.

    Article  CAS  Google Scholar 

  34. P. A. Slepukhin, N. S. Boltacheva, V. I. Filyakova, V. N. Charushin, J. Struct. Chem., 2011, 52, 443; DOI: 0022-4766/11/5202-0443.

    Article  CAS  Google Scholar 

  35. V. I. Filyakova, K. I. Pashkevich, I. Ya. Postovskii, Bull. Acad. Sci. USSR. Div. Chem. Sci., 1981, 30, 2207; DOI: https://doi.org/10.1007/BF01094667.

    Article  Google Scholar 

  36. K. I. Pashkevich, V. I. Filyakova, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1986, 35, 566; DOI: https://doi.org/10.1007/BF00953227.

    Article  Google Scholar 

  37. V. I. Filyakova, I. G. Busygin, K. I. Pashkevich, Zh. Org. Khim. [J. Org. Chem. USSR], 1989, 25, 1865 [ChemInform, 1990, 21]; DOI: https://doi.org/10.1002/chin.199002097.

    CAS  Google Scholar 

  38. V. I. Saloutin, Ya. V. Burgart, Z. E. Skryabina, V. I. Filyakova, Zh. Org. Khim. [J. Org. Chem. USSR], 1995, 31, 54 [ChemInform, 2010, 26(51)]; DOI: https://doi.org/10.1002/chin.199551086.

    CAS  Google Scholar 

  39. K. I. Pashkevich, V. I. Filyakova, I. Ya. Postovskii, Bull. Acad. Sci. USSR. Div. Chem. Sci., 1981, 30, 1931; DOI: https://doi.org/10.1007/BF00963426.

    Article  Google Scholar 

  40. K. I. Pashkevich, A. Ya. Aizikovich, Dokl. Akad. Nauk SSSR [Dokl. Chem.], 1979, 244, 618 (in Russian).

    CAS  Google Scholar 

  41. A. Ya. Aizikovich, M. N. Rudaya, V. V. Mosin, K. I. Pashkevich, I. Ya. Postovskii, Izv. AN SSSR. Ser. Khim. [Bull. Acad. Sci. USSR. Div. Chem. Sci.], 1980, 29, 1939 (in Russian).

    Google Scholar 

  42. A. Ya. Aizikovich, V. V. Gorshkov, M. N. Rudaya, K. I. Pashkevich, I. Ya. Postovskii, Zh. Obshch. Khim. [J. Gen. Chem. USSR], 1980, 50, 1866 (in Russian).

    Google Scholar 

  43. I. G. Busygin, T. A. Sinitsina, A. Ya. Aizikovich, K. I. Pashkevich, Zh. Org. Khim. [J. Org. Chem.. USSR], 1988, 24, 475 (in Russian).

    Google Scholar 

  44. P. A. Slepukhin, N. S. Boltacheva, V. I. Filyakova, V. N. Charushin, Russ. Chem. Bull., 2019, 68, 1213; DOI: https://doi.org/10.1007/s11172-019-2543-y.

    Article  CAS  Google Scholar 

  45. G. M. Sheldrick, Acta Cryst., 2008, A64, 112.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 ul. S. Kovalevskoi, 620108, Yekaterinburg, Russian Federation

    P. A. Slepukhin, N. S. Boltacheva, M. G. Pervova, V. I. Filyakova & V. N. Charushin

Authors
  1. P. A. Slepukhin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. N. S. Boltacheva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. G. Pervova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. I. Filyakova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. V. N. Charushin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. I. Filyakova.

Additional information

The work was performed within the framework of the State assignment (No. AAAA-A19-119012290117-6) using facilities of the Joint Use Center “Spectroscopy and Analysis of Organic Compounds” (JUC SAOC) of the I. Ya. Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Slepukhin, P.A., Boltacheva, N.S., Pervova, M.G. et al. Synthesis and structure of regioisomeric amino enones containing 2-pyridyl and CF3 substituents. Russ Chem Bull 69, 2355–2362 (2020). https://doi.org/10.1007/s11172-020-3030-1

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-020-3030-1

Key words

Search

Navigation