Skip to main content
SpringerLink
Log in

2-Cyano-3-(dimethylamino)prop-2-ene Thioamide: A New Reagent for Synthesis of Functionalized 4-Unsubstituted Ethyl Nicotinates and Nicotinonitriles

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

Condensation of cyclopent(hex)ylidenecyanothioacetamide with N, N-dimethylformamide dimethyl acetal led to the formation of a new reagent for organic synthesis: 2-cyano-3-(dimethylamino)prop-2-ene thioamide. On its basis a series of ethyl nicotinates and nicotinonitriles were synthesized by a vinyl substitution reaction.

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. Elgemeie, G.E.H., Regaila, H.A., and Shehata, N., J. Chem. Soc. Perkin Trans. 1, 1990, no. 5, p. 1267. doi https://doi.org/10.1039/P19900001267

  2. Dyachenko, V.D., Mitroshin, A.E., and Litvinov, V.P., Chem. Heterocycl. Compd., 1996, vol. 32, no. 9, p. 1058. doi https://doi.org/10.1007/BF01164713

    Article  Google Scholar 

  3. Dyachenko, A.D., Desenko, S.M., Dyachenko, V.D., and Rusanov, E.B., Chem. Heterocycl. Compd., 2003, vol. 39, no. 6, p. 744. doi https://doi.org/10.1023/A:1025690927825

    Article  CAS  Google Scholar 

  4. Dyachenko, V.D. and Litvinov, V.P., Chem. Heterocycl. Compd., 1998, vol. 34, no. 2, p. 183. doi https://doi.org/10.1007/BF02315181

    Article  CAS  Google Scholar 

  5. Dyachenko, A.D., Rusanov, E.B., Dyachenko, V.D., Chernega, A.N., and Desenko, S.M., Chem. Heterocycl. Compd., 2003, vol. 39, no. 10, p. 1369. doi https://doi.org/10.1023/B:COHC.0000010655.77713.17

    Article  CAS  Google Scholar 

  6. Magerramov, A.M., Shikhaliev, N.G., Dyachenko, V.D., Dyachenko, I.V., and Nenaidenko, V.G., α-Thianotioatsetamid (α-Cyanothioacetamide), Moscow: Tekhnosfera, 2018.

    Google Scholar 

  7. Warshakoon, N.C. and Buch, R.D., US Patent 6930117, 2005.

  8. Mohamed, S.F., Youssef, M.M., Amr, A.E.-G., and Kotb, E.R., Sci. Pharm., 2008, vol. 76, p. 279. doi https://doi.org/10.3797/scipharm.0804-09

    Article  CAS  Google Scholar 

  9. Zink, M., Lanig, H., and Troschuetz, R., Eur. J. Med. Chem., 2004, vol. 39, p. 1079. doi https://doi.org/10.1016/j.ejmech.2004.09.001

    Article  CAS  PubMed  Google Scholar 

  10. Furstner, A., Waldmann, H., Feyen, F., and Prinz, H., Germany Patent 10345648, 2005.

  11. Renhowe, P.A., Machajewski, T., Shafer, C., Mary, E.W., and Pecchi, S., US Patent 7138409, 2006.

  12. Mizuta, E., Kuno, S., Hanada, T., and Ueno, M., Japan Patent 1875912, 2008.

  13. Rouf, A. and Tanyeli, C., Eur. J. Med. Chem., 2015, vol. 97, p. 911. doi https://doi.org/10.1016/j.ejmech.2014.10.058

    Article  CAS  PubMed  Google Scholar 

  14. Frija, L.M.T., Pombeiro, A.J.L., and Kopylovich, M.N., Coord. Chem. Rev., 2016, vol. 308, p. 32. doi https://doi.org/10.1016/j.ccr.2015.10.003

    Article  CAS  Google Scholar 

  15. Kuroda, N., Nara, Y., Hashiguchi, S., Tasaka, A., Kusaka, M., Yamaoka, M., and Kaku, T., US Patent 7067573, 2006.

  16. Barfacker, L., Kolkhof, P., Schlemmer, K.-H., Grosser, R., and Nitsche, A., Germany Patent 102006044696, 2008.

  17. Dyachenko, V.D., Zh. Org. Farm. Khim., 2012, vol. 10, no. 2, p. 54.

    CAS  Google Scholar 

  18. Yakunin, Ya.Yu. and Dyachenko, V.D., Vestn. Kharkivsk. Nats. Univ.: Khimiya, no. 477, no. 5(28), p. 41.

  19. Tkachev, R.P., Bityukova, O.S., Dyachenko, V.D., Tkacheva, V.P., and Dyachenko, A.D., Russ. J. Gen. Chem., 2007, vol. 77, no. 1, p. 116. doi https://doi.org/10.1134/S1070363207010161

    Article  CAS  Google Scholar 

  20. Dyachenko, V.D., Tkachev, R.P., and Chernega, A.N., Chem. Heterocycl. Compd., 2005, vol. 41, no. 4, p. 503. doi https://doi.org/10.1007/s10593-005-0179-3

    Article  CAS  Google Scholar 

  21. Dyachenko, I.V. and Dyachenko, V.D., Russ. J. Org. Chem., 2015, vol. 51, no. 9, p. 1293. doi https://doi.org/10.1134/S1070428015090146

    Article  CAS  Google Scholar 

  22. Dyachenko, V.D. and Tkachev, R.P., Russ. J. Org. Chem., 2003, vol. 39, no. 8, p. 1174. doi https://doi.org/10.1023/B:RUJO.0000010189.83376.ca

    Article  CAS  Google Scholar 

  23. Pretch, E., Bühlmann, P., and Affolter, C., Structure Determination of Organic Compounds: Tables of Spectral Data, Berlin: Springer, 2000.

    Book  Google Scholar 

  24. Zaikin, V.G., Varlamov, A.V., and Mikaya, A.I., Osnovy mass-spektrometrii organicheskikh soedinenii (Mass Spectrometry of Organic Compounds), Moscow: MAIK Nauka/Interperiodika, 2001.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Taras Shevchenko Lugansk National University, ul. Oboronnaya 2, Lugansk, 91011, Ukraine

    I. V. Dyachenko

Authors
  1. I. V. Dyachenko
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to I. V. Dyachenko.

Additional information

Russian Text © The Authors(s), 2019, published in Zhurnal Obshchei Khimii, 2019, Vol. 89, No. 5, pp. 701–706.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Dyachenko, I.V. 2-Cyano-3-(dimethylamino)prop-2-ene Thioamide: A New Reagent for Synthesis of Functionalized 4-Unsubstituted Ethyl Nicotinates and Nicotinonitriles. Russ J Gen Chem 89, 896–900 (2019). https://doi.org/10.1134/S1070363219050062

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363219050062

Keywords

Search

Navigation