Selective quasi-hydrolysis of cyano group in 6-hydroxypiperidine-3,4,4-tricarbonitriles

Abstract

Reactions of 3,3-dialkyl-4-oxoalkane-1,1,2,2-tetracarbonitriles with water in the presence of pyruvic acid are accompanied by selective quasi-hydrolysis of cyano groups in intermediate 6-hydroxypiperidine-3,4,4-tricarbonitriles.

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

References

  1. 1.

    Ievlev, M.Yu., Ershov, O.V., Belikov, M.Yu., Milovidova, A.G., Tafeenko, V.A., and Nasakin, O.E., Beilstein J. Org. Chem., 2016, vol. 12, p. 2093.

    CAS  Article  Google Scholar 

  2. 2.

    Ievlev, M.Yu., Ershov, O.V., and Tafeenko, V.A., Org. Lett., 2016, vol. 18, p. 1940.

    CAS  Article  Google Scholar 

  3. 3.

    Ershov, O.V., Lipin, K.V., Eremkin, A.V., Nasakin, O.E., Sheverdov, V.P., Fedorov, V.P., and Tafeenko, V.A., Russ. J. Org. Chem., 2017, vol. 53, p. 215.

    CAS  Article  Google Scholar 

  4. 4.

    Ershov, O.V., Fedoseev, S.V., Belikov, M.Yu., and Ievlev, M.Yu., RSC Adv., 2015, vol. 5, p. 34 191.

    CAS  Article  Google Scholar 

  5. 5.

    Sheverdov, V.P., Ershov, O.V., Nasakin, O.E., Chernushkin, A.N., Tafeenko, V.A., and Firgang, S.I., Tetrahedron, 2001, vol. 57, p. 5815.

    CAS  Article  Google Scholar 

  6. 6.

    Belikov, M.Yu., Ievlev, M.Yu., Belikova, I.V., Ershov, O.V., Tafeenko, V.A., and Surazhskaya, M.D., Chem. Heterocycl. Compd., 2015, vol. 51, p. 518.

    CAS  Article  Google Scholar 

  7. 7.

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

    CAS  Article  Google Scholar 

  8. 8.

    Ievlev, M.Yu., Ershov, O.V., Milovidova, A.G., Belikov, M.Yu., and Nasakin, O.E., Chem. Heterocycl. Compd., 2015, vol. 51, p. 457.

    CAS  Article  Google Scholar 

  9. 9.

    Belikov, M.Yu., Ievlev, M.Yu., Ershov, O.V., Lipin, K.V., Legotin, S.A., and Nasakin, O.E., Russ. J. Org. Chem., 2014, vol. 50, p. 1372.

    CAS  Article  Google Scholar 

  10. 10.

    Ershov, O.V., Lipin, K.V., Maksimova, V.N., Eremkin, A.V., Kayukov, Ya.S., and Nasakin, O.E., Russ. J. Org. Chem., 2009, vol. 45, p. 475.

    CAS  Article  Google Scholar 

  11. 11.

    Ershov, O.V., Lipin, K.V., and Nasakin, O.E., Russ. J. Org. Chem., 2016, vol. 52, p. 970.

    CAS  Article  Google Scholar 

  12. 12.

    Ershov, O.V., Ievlev, M.Yu., Belikov, M.Yu., Lipin, K.V., Naydenova, A.I., and Tafeenko, V.A., RSC Adv., 2016, vol. 6, p. 82 227.

    CAS  Article  Google Scholar 

  13. 13.

    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.

    CAS  Article  Google Scholar 

  14. 14.

    Belikov, M.Yu., Ershov, O.V., Eremkin, A.V., Kayukov, Ya.S., and Nasakin, O.E., Russ. J. Gen. Chem., 2010, vol. 80, p. 2078.

    CAS  Article  Google Scholar 

  15. 15.

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

    CAS  Article  Google Scholar 

Download references

Author information

Affiliations

Authors

Corresponding author

Correspondence to K. V. Lipin.

Additional information

Original Russian Text © K.V. Lipin, S.V. Fedoseev, O.V. Ershov, V.A. Tafeenko, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 12, pp. 1792–1796.

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Lipin, K.V., Fedoseev, S.V., Ershov, O.V. et al. Selective quasi-hydrolysis of cyano group in 6-hydroxypiperidine-3,4,4-tricarbonitriles. Russ J Org Chem 53, 1828–1832 (2017). https://doi.org/10.1134/S1070428017120077

Download citation