Skip to main content
SpringerLink
Log in

Chemoselective Alkylation of 3- and 4-(5-Amino-4-hetaryl-2,3-dihydro-3-oxopyrrol-1-yl)benzoic Acids

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

Abstract

Alkylation of 3- and 4-(5-amino-4-hetaryl-2,3-dihydro-3-oxopyrrol-1-yl)benzoic acids with phenacyl bromides or chloroacetanilides in DMF in the presence of triethylamine occurs at the carboxy group with high selectivity and yields the corresponding phenacyl and arylcarbamoylmethyl esters. The initial pyrrolylbenzoic acids were synthesized by reaction of 3- and 4-aminobenzoic acids with 4-chloro-2-hetaryl-3-oxo-butyronitriles.

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. Babichev, F.S. and Volovenko, Yu.M., Khim. Geterotsikl. Soedin., 1977, no. 4, p. 557.

  2. Volovenko, Yu.M., Gofman, L.V., and Babichev, F.S., Ukr. Khim. Zh., 1979, vol. 45, p. 857.

    Google Scholar 

  3. Volovenko, Yu.M., Shokol, T.V., Merkulov, A.S., and Babichev, F.S., Ukr. Khim. Zh., 1993, vol. 59, p. 55.

    Google Scholar 

  4. Tverdokhlebov, A.V., Volovenko, Yu.M., and Shokol, T.V., Khim. Geterotsikl. Soedin., 1998, no. 1, p. 50.

  5. Resnyanskaya, E.V., Shokol, T.V., Volovenko, Yu.M., and Tverdokhlebov, A.V., Khim. Geterotsikl. Soedin., 1999, no. 10, p. 1412.

  6. Volovenko, Yu.M., Volovnenko, T.A., Tverdokhlebov, A.V., and Ryabokon', I.G., Russ. J. Org. Chem., 2001, vol. 37, p. 1323.

    Google Scholar 

  7. Volovenko, Yu.M., Tverdokhlebov, A.V., Gorulya, A.P., Shishkina, S.V., Zubatyuk, R.I., and Shishkin, O.V., Eur. J. Org. Chem., 2002, p. 663.

  8. Resnyanskaya, E.V., Tverdokhlebov, A.V., Volovenko, Yu.M., Shishkin, O.V., and Zubatyuk, R.I., Synthesis, 2002, p. 2717.

  9. Gola, A., Samartzi, E., Bardakos, V., Petroliagi, M., Igglessi-Markopoulou, O., Markopoulos, J., and Barkley, J.V., J. Heterocycl. Chem., 2000, vol. 37, p. 681.

    Google Scholar 

  10. Missbach, M., PCT Int. Appl. WO 9 610 028, 1996; Chem. Abstr., 1996, vol. 125, no. 86 670.

  11. Aso, K., Hitaka, T., Yukishige, K., Ootsu, K., and Akimoto, H., Chem. Pharm. Bull., 1995, vol. 43, p. 256.

    Google Scholar 

  12. Akimoto, H., Hitaka, T., and Miwa, T., Eur. Pat. Appl. EP 400 562, 1990; Chem. Abstr., 1991, vol. 115, no. 29 914.

  13. Volovenko, Yu.M., Volovnenko, T.A., and Tverdokhlebov, A.V., Khim. Geterotsikl. Soedin., 2001, no. 8, p. 1101.

  14. Shriner, R.L., Fuson, R.C., Curtin, D.Y., and Morrill, T.C., The Systematic Identification of Organic Compounds. A Laboratory Manual, New York: Wiley, 1978. Translated under the title Analiz organicheskikh soedinenii, Moscow: Mir, 1983, p. 311.

    Google Scholar 

  15. Ward, C.E., J. Chem. Soc., 1923, vol. 123, p. 2211.

    Google Scholar 

  16. Balls, A.K. and Kohler, F., Chem. Ber., 1931, vol. 64, p. 34.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Taras Shevchenko Kiev National University, ul. Vladimirskaya 62, Kiev, 01033, Ukraine

    E. V. Resnyanskaya, A. V. Tverdokhlebov, Yu. M. Volovenko & T. V. Shokol

Authors
  1. E. V. Resnyanskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. V. Tverdokhlebov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yu. M. Volovenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. T. V. Shokol
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Resnyanskaya, E.V., Tverdokhlebov, A.V., Volovenko, Y.M. et al. Chemoselective Alkylation of 3- and 4-(5-Amino-4-hetaryl-2,3-dihydro-3-oxopyrrol-1-yl)benzoic Acids. Russian Journal of Organic Chemistry 40, 368–371 (2004). https://doi.org/10.1023/B:RUJO.0000034973.29561.7c

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/B:RUJO.0000034973.29561.7c

Keywords

Search

Navigation