Skip to main content
Log in

Tricomponent domino synthesis of 6-hydroxy-2-chloro-1,4,5,6-tetrahydropyridine-3,4,4-tricarbonitriles

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

Abstract

In reaction of tetracyanoethylene with ketones and HCl in 1,4-dioxane at 30–40°? 6-hydroxy-2-chloro-1,4,5,6-tetrahydropyridine-3,4,4-tricarbonitriles are formed.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Ershov, O.V., Ievlev, M.Yu., Tafeenko, V.A., and Nasakin, O.E., Green Chem., 2015, vol. 17, p. 4234. doi 10.1039/C5GC00909J

    Article  CAS  Google Scholar 

  2. Ievlev, M.Yu., Ershov, O.V., Milovidova, A.G., Belikov, M.Yu., and Nasakin, O.E., Chem. Heterocycl. Compd., 2015, vol. 51, p. 457. doi 10.1007/s10593-015-1720-7

    Article  CAS  Google Scholar 

  3. Eremkin, A.V., Ershov, O.V., Mol’kov, S.N., Sheverdov, V.P., Nasakin, O.E., Kayukov, Ya.S., and Tafeenko, V.A., Russ. J. Org. Chem., 2006, vol. 42, p. 193. doi 10.1134/S1070428002120060

    Article  CAS  Google Scholar 

  4. Ershov, O.V., Eremkin, A.V., Kayukov, Ya.S., Nasakin, O.E., Tafeenko, V.A., and Nurieva, E.V., Tetrahedron Lett., 2017, vol. 48, p. 2803. doi 10.1016/j.tetlet.2007.01.138

    Article  Google Scholar 

  5. Sheverdov, V.P., Ershov, O.V., Nasakin, O.E., Chernushkin, A.N., and Tafeenko, V.A., Russ. J. Org. Chem., 2002, vol. 38, p. 1001. doi 10.1023/A:1020801612443

    Article  CAS  Google Scholar 

  6. Ershov, O.V., Lipin, K.V., Eremkin, A.V., Kayukov, Ya.S., and Nasakin, O.E., Russ. J. Org. Chem., 2009, vol. 45, p. 470. doi 10.1134/S1070428009030245

    Article  CAS  Google Scholar 

  7. Nasakin, O.E., Sheverdov, V.P., Ershov, O.V., Moiseeva, I.V., Lyshchikov, A.N., Khrustalev, V.N., and Antipin, M.Yu., Mendeleev Commun., 1997, vol. 7, p. 112. doi 10.1070/MC1997v007n03ABEH000722

    Article  Google Scholar 

  8. Bardasov, I.N., Alekseeva, A.U., Mihailov, D.L., Ershov, O.V., Nasakin, O.E., and Tafeenko, V.A., Tetrahedron Lett., 2014, vol. 55, p. 2730. doi 10.1016/j.tetlet.2014.03.056

    Article  CAS  Google Scholar 

  9. Eremkin, A.V., Molkov, S.N., Ershov, O.V., Kayukov, Ya.S., Nasakin, O.E., Tafeenko, V.A., and Nurieva, E.V., Mendeleev Commun., 2006, vol. 15, p. 115. doi 10.1070/MC2006v016n02ABEH002206

    Article  Google Scholar 

  10. Lu, S., Shao, X., Li, Zh., Xu, Zh., Zhao, Sh., Wu, Y., and Xu, X., J. Agric. Food Chem., 2012, vol. 60, p. 322. doi 10.1021/jf203068a

    Article  CAS  Google Scholar 

  11. Carroll, W.A., Agrios, K.A., Altenbach, R.J., Buckner, S.A., Chen, Y., Coghlan, M.J., Daza, A.V., Drizin, I., Gopalakrishnan, M., Henry, R.F., Kort, M.E., Kym, P.R., Milicic, I., Smith, J.C., Tang, R., Turner, S.C., Whiteaker, K.L., Zhang, H., and Sullivan, J.P., J. Med. Chem., 2004, vol. 47, p. 3180. doi 10.1021/jm030357o

    Article  CAS  Google Scholar 

  12. Kandil, S., Wymant, J.M., Kariuki, B.M., Jones, A.T., McGuigan, C., and Westwell, A.D., Eur. J. Med. Chem., 2016, vol. 110, p. 311. doi 10.1016/j.ejmech.2015.12.037

    Article  CAS  Google Scholar 

  13. Iwasawa, T., Hooley, R.J., and Rebek, J., Science, 2007, vol. 317, p. 493. doi 10.1126/science.1143272

    Article  CAS  Google Scholar 

  14. Sheldrick, G.M., Acta Cryst., Sect. A, 2008, vol. 64, p. 112. doi 10.1107/S0108767307043930

    Article  CAS  Google Scholar 

  15. Brandenburg, K., DIAMOND, Release 2.1d, Germany, Bonn Crystal Impact, 2000.pb]Nauka/Interperiodica Moscow

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to O. V. Ershov.

Additional information

Original Russian Text © K.V. Ershov, K.V. Lipin, O.V. Eremkin, O.E. Nasakin, V.P. Sheverdov, P.I. Fedorov, V.E. Tafeenko, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 2, pp. 223–228.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ershov, O.V., Lipin, K.V., Eremkin, A.V. et al. Tricomponent domino synthesis of 6-hydroxy-2-chloro-1,4,5,6-tetrahydropyridine-3,4,4-tricarbonitriles. Russ J Org Chem 53, 215–221 (2017). https://doi.org/10.1134/S1070428017020129

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428017020129

Navigation