Skip to main content
SpringerLink
Log in

The Reactivity Trends in Electrochemical Chlorination and Bromination of N-Substituted and N-Unsubstituted Pyrazoles*

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Our investigation of electrochemical chlorination and bromination of pyrazoles decorated with electron-withdrawing and electron-donating groups showed that the product yield and composition depended on the substitution at the N-1 atom. We have shown for the first time the significant differences in halogenation reactivity patterns of N-unsubstituted and N-alkylpyrazoles.

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. E. M. Borroni, G. Huber-Trottmann, G. J. Kilpatrick, and R. D. Norcross, WO Pat. Appl. 0162233.

  2. J. U. Smallheer and J. R. Corte, US Pat. Appl. 2005228000.

  3. A. G. Taveras, C. J. Aki, R. W. Bond, J. Chao, M. Dwyer, J. A. Ferreira, J. Chao, Y. Yu, J. J. Baldwin, B. Kaiser, G. Li, J. R. Merritt, P. J. Biju, K. H. Nelson, L. L. Rokosz, J. P. Jakway, G. Lai, M. Wu, E. A. Hecker, D. Lundell, and J. S. Fine, US Pat. Appl. 2004147559.

  4. I. Yoshida, N. Yoneda, Y. Ohashi, S. Suzuki, M. Miyamoto, F. Miyazaki, H. Seshimo, J. Kamata, Y. Takase, M. Shirato, D. Shimokubo, Y. Sakuma, and H. Yokohama, WO Pat. Appl. 02088107.

  5. W. Schaper, H. Bastiaans, S. Harmsen, U. Doeller, J. Tiebes, D. Jans, W. Hempel, U. Sanft, and M.-T. Thoenessen, DE Pat. Appl. 19962901; Chem. Abstr., 135, 76877 t (2001).

    Google Scholar 

  6. K. Eicken, W. Rohr, B. Zeeh, and B. Wuerzer, DE Pat. Appl. 2648008; Chem. Abstr., 89, 109503e (1978).

    Google Scholar 

  7. S. F. Vasilevsky, S. V. Klyatskaya and J. Elguero, Tetrahedron, 60, 6685 (2004).

    Article  CAS  Google Scholar 

  8. J. Elguero, C. Jaramilo, and C. Pardo, Synthesis, 563 (1997).

  9. V. Collot, P. Dallemagnet, and P. P. Bovy, Tetrahedron, 59, 6917 (1999).

    Article  Google Scholar 

  10. B. V. Lyalin, V. A. Petrosyan, and B. I. Ugrak, Elektrokhimiya, 44, 1418 (2008). [Russ. J. Electrochem., 44, 1320 (2008).]

    Google Scholar 

  11. B. V. Lyalin, V. A. Petrosyan, and B. I. Ugrak, Izv. Akad. Nauk, Ser. Khim., 291 (2009). [Russ. Chem. Bull., Int. Ed., 58, 291 (2009).]

    Google Scholar 

  12. B. V. Lyalin, V. A. Petrosyan, and B. I. Ugrak, Elektrokhimiya, 46, 131 (2010). [Russ. J. Electrochem., 46, 123 (2010).]

    Google Scholar 

  13. H. G. O. Beсker, Einfűhrung in die Electronentheorie Organisch-Chemisher Reactionen, Veb Deutsher Verlag der Wissenshaften, Berlin (1974)

    Google Scholar 

  14. B. E. Boulton and B. A. W. Coller, Aust. J. Chem., 24, 1413 (1971).

    Article  CAS  Google Scholar 

  15. J. D. Vaughan, D. G. Lambert, and V. L. Vaughan, J. Am. Chem. Soc., 86, 2857 (1964).

    Article  CAS  Google Scholar 

  16. M. S. Pevzner, Adv. Heterocycl. Chem., 75, 1 (1999).

    Article  CAS  Google Scholar 

  17. B. V. Lyalin, V. A. Petrosyan, and B. I. Ugrak, Izv. Akad. Nauk, Ser. Khim., 1512 (2010). [Russ. Chem. Bull., Int. Ed., 59, 1549 (2010).]

    Google Scholar 

  18. L. I. Belen'kii and N. D. Chuvylkin, Khim. Geterotsikl. Soedin., 1535 (1996). [Chem. Heterocycl. Compd., 32, 1319 (1996).]

    Google Scholar 

  19. R. Hüttel, О. Schäfe and G. Welzee, Justus Liebigs Ann. Chem., 598, 186 (1956).

    Article  Google Scholar 

  20. R. Hüttel, H. Wagner and P. Jocum, Justus Liebigs Ann. Chem., 593, 179 (1955).

    Article  Google Scholar 

  21. B. V. Lyalin and V. A. Petrosyan, Izv. Akad. Nauk, Ser. Khim., 206 (2012). [Russ. Chem. Bull., Int. Ed., 61, 209 (2012).]

  22. A. E. Agronomov, Selected topics of organic chemistry, Khimiya, Moscow (1990), p. 329.

    Google Scholar 

  23. P. G. Baraldi, P. Cozzi, C. Geroni, N. Mongelli, R. Romagnoli, and G. Spalluto, Bioorg. Med. Chem., 7, 251 (1999).

    Article  CAS  Google Scholar 

  24. S. F. Vasilevsky and M. S. Shvartsberg, Izv. Akad. Nauk SSSR, Ser. Khim., 1071 (1980). [Bull. Acad. Sci. USSR, Div. Chem. Sci., 29, 778 (1980).]

  25. P. R. Mullens, Tetrahedron Lett., 50, 6783 (2009).

    Article  CAS  Google Scholar 

  26. J. L. Huppatz and L. John, Aust. J. Chem., 36, 135 (1983).

    Article  CAS  Google Scholar 

  27. A. A. Zaitsev, I. L. Dalinger, A. M. Starosotnikov, T. K. Shkineva, and S. A. Shevelev, Zh. Org. Khim., 41, 1538 (2005). [Russ. J. Org. Chem., 41, 1507 (2005).]

    Google Scholar 

  28. V. P. Perevalov, Yu. A. Manayev, L. I. Baryshnenkova, E. E. Kanep, M. A. Andreeva, and B. I. Stepanov, Khim. Geterotsikl. Soedin., 1350 (1987). [Chem. Heterocycl. Compd., 23, 1081 (1987).]

    Google Scholar 

  29. V. P. Perevalov, L. I. Baryshnenkova, M. A. Andreeva, Yu. A. Manaev, I. A. Denisova, B. I. Stepanov, and V. I. Seraya, Khim. Geterotsikl. Soedin., 1672 (1983). [Chem. Heterocycl. Compd., 19, 1322 (1983).]

    Google Scholar 

  30. O. S. Attaryan, G. A. Akopyan, K. S. Badalyan, and G. V. Astratyan, Zh. Org. Khim., 43, 1739 (2007). [Russ. J. Org. Chem., 43, 1740 (2007).]

    Google Scholar 

  31. M. A. Andreeva, A. K. Karim, E. A. Denisova, V. P. Perevalov, and B. I. Stepanov, Zh. Obsch. Khim., 50, 2116 (1980). [Russ. J. Gen. Chem., 50, 2370 (1980).]

    CAS  Google Scholar 

  32. B. I. Stepanov, V. P. Perevalov, M. A. Andreeva, and A. K. Karim, Zh. Obsch. Khim., 52, 2588 (1982). [Russ. J. Gen. Chem., 52, 2588 (1982).]

    CAS  Google Scholar 

  33. J. Pelleter and F. Renaud, Org. Process Res. Dev., 13, 698 (2009).

    Article  CAS  Google Scholar 

  34. J. Elguero, R. Jacquier, and H. C. N. Tien Duc, Bull. Soc. Chim. Fr., 3727 (1966).

  35. Y. Iwasawa, S. Yamamoto, K. Suzuki, H. Murakami, and F. Suzuki, EP Pat. Appl. 0366329.

Download references

Author information

Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow, 119991, Russia

    B. V. Lyalin & V. A. Petrosyan

Authors
  1. B. V. Lyalin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. A. Petrosyan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to B. V. Lyalin.

Additional information

*Dedicated to my dear friend Jānis Stradiņš, a uniquely talented scientist, with the warmest greetings and memories of unforgettable adventures in the field of polarography.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1726-1738, November, 2013.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Lyalin, B.V., Petrosyan, V.A. The Reactivity Trends in Electrochemical Chlorination and Bromination of N-Substituted and N-Unsubstituted Pyrazoles*. Chem Heterocycl Comp 49, 1599–1610 (2014). https://doi.org/10.1007/s10593-014-1411-9

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-014-1411-9

Keywords

Search

Navigation