Skip to main content
SpringerLink
Log in

New approach to the preparation of p-(1-cyanoethyl)arenesulfonamides by reaction of arylsulfonyl imines of polychloroacetaldehydes with acetone cyanohydrin

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

Abstract

Reaction of N-(2,2,2-trichloroethylidene)- or N-(1-phenyl-2,2-dichloroethylidene)arenesulfonamides with acetone cyanohydrin in acetone in the presence of potassium carbonate led to the formation of N- (2,2,2-trichloro-1-cyanoethyl)- or N-(2-phenyl-2,2-dichloro-1-cyanoethyl)arenesulfonamides.

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. Levkovskaya, G.G., Drozdova, T.I., Rozentsveig, I.B., and Mirskova, A.N., Russ. Chem. Rev., 1999, vol. 68, p. 581. doi 10.1070/RC1999v068n07ABEH000476

    Article  CAS  Google Scholar 

  2. DeKimpe, N. and Verhé, R., The Chemistry of α-Haloketones, α-Haloaldehydes and α-Haloimines, Chichester: Wiley, 1988.

    Book  Google Scholar 

  3. Rozentsveig, I.B., Rozentsveig, G.N., Serykh, V.Yu., Chernyshev, K.A., and Levkovskaya, G.G., Eur. J. Org. Chem., 2011, vol. 23, p. 4415.

    Article  Google Scholar 

  4. Rozentsveig, I.B., Serykh, V.Yu., Chernysheva, G.N., Chernyshev, K.A., Kondrashov, E.V., Tretyakov, E.V., and Romanenko, G.V., Eur. J. Org. Chem., 2013, vol. 2, p. 368.

    Article  Google Scholar 

  5. Rozentsveig, I.B., Serykh, V.Yu., Chernysheva, G.N., Kondrashov, E.V., Fedotova, A.I., Ushakov, I.A., Tretyakov, E.V., and Romanenko, G.V., Eur. J. Org. Chem., 2014, vol. 29, p. 6547.

    Article  Google Scholar 

  6. Serykh, V.Y., Chernysheva, G.N., Kondrashov, E.V., Vashchenko, A.V., Smirnov, V.I., and Rozentsveig, I.B., Arkivoc, 2015, vol. VII, p.377.

    Google Scholar 

  7. Rozentsveig, I.B., Popov, A.V., Rozentsveig, G.N., Serykh, V.Yu., Chernyshev, K.A., Krivdin, L.B., and Levkovskaya, G.G., Mol. Div., 2010, vol. 14, p. 533.

    Article  CAS  Google Scholar 

  8. Rozentsweig, I.B., Popov, A.V., Brikov, A.V., Mirskova, A.N., and Levkovskaya, G.G., Russ. J. Org. Chem., 2007, vol. 43, p. 780. doi 10.1134/S1070428007050260

    Article  CAS  Google Scholar 

  9. Mirskova, A.N., Rudyakova, E.V., Rozentsveig, I.B., Stupina, A.G., Levkovkskaya, G.G., and Albanov, A.I., Pharm. Chem. J., 2001, vol. 35, p. 312. doi 10.1023/A:1012341604254

    Article  Google Scholar 

  10. Drach, B.S. and Mis’kevich, G.N., Zh. Org. Chem., 1976, vol. 12, p. 465.

    CAS  Google Scholar 

  11. Drach, B.S., Brovarets, B.S., and Stolii, O.B., Sintezy azotsoderzhashchikh geterorsiklicheskikh soedinenii na osnove amidoalkiliruyushchikh agentov (Synthesis of Nitrogen-containing Heterocyclic Compounds Based on Amidoalkylating Agents), Kiev: Naukova Dumka, 1992.

    Google Scholar 

  12. Drach, B.S., Sviridov, E.P., Kisilenko, A.A., and Kirsanov, A.V., Zh. Org. Khim., 1973, vol. 9, p. 1818.

    CAS  Google Scholar 

  13. Drach, B.S., Sviridov, E.P., and Lavrenyuk, T.Ya., Zh. Org. Khim., 1974, vol. 10, p. 1271.

    CAS  Google Scholar 

  14. March, J., Advanced Organic Chemistry. Reactions, Mechanisms, and Structure, New York: Wiley, 1985. Translated under the title Organicheskaya khimiya. Reaktsii, mekhanizmy i struktura, Moscow: Mir, 1987, vol. 3, p. 458.

    Google Scholar 

  15. Mirskova, A.N., Levkovskaya, G.G., Drozdova, T.I., Kalikhman, I.D., and Voronkov, M.G., Zh. Org. Khim., 1982, vol. 18, p. 452.

    CAS  Google Scholar 

  16. Rozentsveig, I.B., Rozentsveig, G.N., Mirskova, A.N., Chernyshev, K.A., Krivdin, L.B., and Levkovskaya, G.G., Russ. J. Gen. Chem., 2008, vol. 78, p. 1371. doi 10.1134/S1070363208070141

    Article  CAS  Google Scholar 

  17. Mirskova, A.N., Drozdova, T.I., Levkovskaya, G.G., Bannikova, O.B., Kalikhman, I.D., and Voronkov, M.G., Zh. Org. Khim., 1982, vol. 18, p. 1407.

    CAS  Google Scholar 

  18. Drozdova, T.I., Levkovskaya, G.G., and Mirskova, A.N., Zh. Org. Khim., 1992, vol. 28, p. 1236.

    CAS  Google Scholar 

  19. Labeish, N.N., Porfir’eva, Yu.I., and Petrov, A.A., Zh. Org. Khim., 1985, vol. 21, p. 659.

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    A. R. Kaliev, V. Yu. Serykh & I. B. Rosentsveig

Authors
  1. A. R. Kaliev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. Yu. Serykh
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. I. B. Rosentsveig
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to I. B. Rosentsveig.

Additional information

Original Russian Text © A.R. Kaliev, V.Yu. Serykh, I.B. Rosentsveig, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 8, pp. 1177–1180.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kaliev, A.R., Serykh, V.Y. & Rosentsveig, I.B. New approach to the preparation of p-(1-cyanoethyl)arenesulfonamides by reaction of arylsulfonyl imines of polychloroacetaldehydes with acetone cyanohydrin. Russ J Org Chem 53, 1191–1194 (2017). https://doi.org/10.1134/S1070428017080061

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428017080061

Search

Navigation