Skip to main content
SpringerLink
Log in

Synthesis of N-arylsulfonyl-2-aryl(hetaryl)aminoacetic acids

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

Abstract

Hydrolytic transformations of 4-[2,2,2-trichloro-1-(arylsulfonylamino)-and-(ethoxycarbonylamino)ethyl]phenyloxy(or sulfanyl)acetic acids under microwave irradiation in alkaline medium involve both trichloromethyl group and ester fragment to give N-arylsulfonyl-2-[4-carboxymethyloxy(or sulfanyl)phenyl]-2-aminoacetic acids in good yields. Hydrolysis of methyl 4-[2,2,2-trichloro-1-(arylsulfonylamino)ethyl]phenyloxy(or sulfanyl)acetates without microwave activation occurs only at the ester group with quantitative formation of 4-[2,2,2-trichloro-1-(arylsulfonylamino)ethyl]phenyloxy(or sulfanyl) acetic acids. N-[2,2,2-Trichloro-1-(1-naphthyl, 2-furyl, and 1-methylindol-3-yl)ethyl]-4-chlorobenzenesulfonamides in alkaline medium under microwave irradiation were converted in 10–15 min into the corresponding N-(4-chlorophenylsulfonyl)-2-aryl-2-aminoacetic acids in preparative yields.

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., Usp. Khim., 1999, vol. 68, p. 638.

    Google Scholar 

  2. Levkovskaya, G.G., Evstaf’eva, I.T., Mirskova, A.N., Zhuravlev, S.N., and Kul’nevich, V.G., Zh. Org. Khim., 1987, vol. 23, p. 1991.

    CAS  Google Scholar 

  3. Rozentsveig, I.B., Levkovskaya, G.G., and Mirskova, A.N., Russ. J. Org. Chem., 1999, vol. 35, p. 895.

    CAS  Google Scholar 

  4. Rozentsveig, I.B., Levkovskaya, G.G., Albanov, A.I., and Mirskova, A.N., Russ. J. Org. Chem., 2000, vol. 36, p. 671.

    CAS  Google Scholar 

  5. Levkovskaya, G.G., Krivonos, E.V., Rozentsveig, I.B., Mirskova, A.N., and Albanov, A.I., Russ. J. Org. Chem., 2000, vol. 36, p. 240.

    CAS  Google Scholar 

  6. Rudyakova, E.V., Levkovskaya, G.G., Rozentsveig, I.B., Mirskova, A.N., and Albanov, A.I., Russ. J. Org. Chem., 2003, vol. 39, p. 1753.

    Article  CAS  Google Scholar 

  7. Aizina, Yu.A., Rozentsveig, I.B., Levkovskaya, G.G., Rozentsveig, G.N., and Mirskova, A.N., Russ. J. Org. Chem., 2002, vol. 38, p. 235.

    Article  CAS  Google Scholar 

  8. Levkovskaya, G.G., Rudyakova, E.V., Rozentsveig, I.B., Mirskova, A.N., and Albanov, A.I., Russ. J. Org. Chem., 2000, vol. 36, p. 1338.

    CAS  Google Scholar 

  9. Aizina, Yu.A., Rozentsveig, I.B., Ushakova, I.A., Levkovskaya, G.G., and Mirskova, A.N., Russ. J. Org. Chem., 2005, vol. 41, p. 91.

    Article  CAS  Google Scholar 

  10. Rozentsveig, I.B., Levkovskaya, G.G., Mirskova, A.N., and Kashik, T.V., Russ. J. Org. Chem., 2000, vol. 36, p. 1760.

    CAS  Google Scholar 

  11. Mirskova, A.N., Rudyakova, E.V., Rozentsveig, I.B., Stupina, A.G., Levkovskaya, G.G., and Albanov, A.I., Khim.-Farm. Zh. 2001, no. 6, p. 21.

Download references

Author information

Authors and Affiliations

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

    E. V. Rudyakova, I. T. Evstaf’eva, I. B. Rozentsveig, A. N. Mirskova & G. G. Levkovskaya

Authors
  1. E. V. Rudyakova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. I. T. Evstaf’eva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. I. B. Rozentsveig
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. N. Mirskova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. G. G. Levkovskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Original Russian Text © E.V. Rudyakova, I.T. Evstaf’eva, I.B. Rozentsveig, A.N. Mirskova, G.G. Levkovskaya, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 7, pp. 1001–1005.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Rudyakova, E.V., Evstaf’eva, I.T., Rozentsveig, I.B. et al. Synthesis of N-arylsulfonyl-2-aryl(hetaryl)aminoacetic acids. Russ J Org Chem 42, 981–985 (2006). https://doi.org/10.1134/S1070428006070098

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428006070098

Keywords

Search

Navigation