Skip to main content
Log in

The rate of cyclization of 2′- and 4′-substituted diphenylamine-2-carboxylic acids in sulfuric acid as a function of the electronic properties of substituents

  • Brief Communications
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

The kinetic regularities of cyclization of 2′- and 4′-substituted diphenylamine-2-carboxylic acids in sulfuric acid were determined. The rate of cyclization of diphenylamine-2-carboxylic acids is linearly dependent on the nature of substituents in the meta-position relative to the reaction site in accordance with the two-parameter Hammett equation.

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.

References

  1. E. G. Deeva, Ya. V. Pavlovskaya, O. I. Kiselev, Vestn. Ross. Akad. Med. Nauk [Bull. Russ. Acad. Med. Sci.], 2004, 29 (in Russian).

  2. Y. Hagiwara, T. Hasegawa, A. Shoji, M. Kuwahara, H. Ozaki, H. Sawai, Bioorg. Med. Chem., 2008, 16, 7013.

    Article  CAS  Google Scholar 

  3. A. Shoji, T. Hasegawa, M. Kuwahara, H. Ozaki, H. Sawai, Bioorg. Med. Chem. Lett., 2007, 17, 776.

    Article  CAS  Google Scholar 

  4. O. Tabarrini, V. Cecchetti, A. Fravolini, G. Nocentini, A. Barzi, S. Sabatini, H. Miao, C. Sissi, J. Med. Chem., 1999, 42, 2136.

    Article  CAS  Google Scholar 

  5. J. Reisch, H. M. T. B. Herath, N. S. Kumar, Liebigs Ann. Chem., 1991, 839.

  6. N. Dodic, B. Dumaitre, M. Daugan, P. Pianetti, J. Med. Chem., 1995, 38, 2418.

    Article  CAS  Google Scholar 

  7. W. M. Cholody, B. Horowska, J. Paradziej-Lukowicz, S. Martelli, J. Konopa, J. Med. Chem., 1996, 39, 1028.

    Article  CAS  Google Scholar 

  8. RF Pat. 2020941; Byull. izobret. [Invent. Bull.], 1994, 19 (in Russian).

  9. RF Pat. 2162843; Byull. izobret. [Invent. Bull.], 1994, 19 (in Russian).

  10. RF Pat. 2182004; Byull. izobret. [Invent. Bull.], 2002, 13 (in Russian).

  11. RF Pat. 2197248; Byull. izobret. [Invent. Bull.], 2003, 3 (in Russian).

  12. RF Pat. 2080108; Byull. izobret. [Invent. Bull.], 1997, 15 (in Russian).

  13. Z. Szulz, J. Prakt. Chem., 1987, 329, 741.

    Article  Google Scholar 

  14. RF Pat. 2036198; Byull. izobret. [Invent. Bull.], 1995, 15 (in Russian).

  15. A. A. Auzi, T. G. Hartley, R. D. Waigh, P. G. Waterma, Phytochemistry, 1996, 42, 235.

    Article  CAS  Google Scholar 

  16. T.-S. Wu, S.-C. Huang, P.-L. Wu, Phytochemistry, 1996, 42, 221.

    Article  CAS  Google Scholar 

  17. G. Brader, M. Bacher, H. Greger, O. Hofer, Phytochemistry, 1996, 42, 881.

    Article  CAS  Google Scholar 

  18. K. M. Ahua, J.-R. Ioset, A. Ransijn, J. Mauël, S. Mavi, K. Hostettmann, Phytochemistry, 2004, 65, 963.

    Article  CAS  Google Scholar 

  19. A. L. Skaltsounis, S. Mitaku, Alkaloids Chem. Biol., 2000, 54, 259.

    Article  CAS  Google Scholar 

  20. C. F. H. Allen, G. H. W. McKee, Org. Synth., 1939, 19, 6.

    CAS  Google Scholar 

  21. W. A. Denny, G. J. Atwell, G. W. Rewcastle, B. C. Baguley, J. Med. Chem., 1987, 30, 658.

    Article  CAS  Google Scholar 

  22. G. J. Atwell, B. F. Cain, B. C. Baguley, G. J. Finlay, W. A. Denny, J. Med. Chem., 1984, 27, 1481.

    Article  CAS  Google Scholar 

  23. A. Kamal, O. Srinivas, P. Ramulu, G. Ramesh, P. P. Kumar, Bioorg. Med. Chem. Lett., 2004, 14, 4107.

    Article  CAS  Google Scholar 

  24. W. Bader, F. Ullmann, Ann. Chem., 1907, 355, 323.

    Google Scholar 

  25. H. Hoz, F. Ullmann, Annal. Chem., 1907, 355, 352.

    Google Scholar 

  26. Spravochnik khimika [Chemist’s Handbook], v. 3, Khimicheskoe ravnovesie i kinetika, svoistva rastvorov, elektrodnye protsessy [Chemical Equilibrium and Kinetics, Properties of Solutions, Electrode Processes], 2nd ed. revised., Ed. B. P. Nikol’skii, Khimiya, Moscow, 1965, 1010 pp. (in Russian).

  27. N. S. Frumina, M. L. Nikurashina, Metody polucheniya khimicheskikh reactivov and preparatov [Methods for the Preparation of Chemical Reagents and Chemicals], Moscow, Khimiya, 1970, 22, 63 pp. (in Russian).

    Google Scholar 

  28. Yu. D. Markovich, N. A. Pelevin, T. N. Kudryavtseva, D. S. Lotorev, Zav. Labor., 2008, 4, 7 [Ind. Lab. (Engl. Transl.), 2008, 4].

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to N. A. Pelevin.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 577—579, March, 2011.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Pelevin, N.A., Markovich, Y.D., Nazarov, G.V. et al. The rate of cyclization of 2′- and 4′-substituted diphenylamine-2-carboxylic acids in sulfuric acid as a function of the electronic properties of substituents. Russ Chem Bull 60, 590–592 (2011). https://doi.org/10.1007/s11172-011-0092-0

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-011-0092-0

Key words

Navigation