Skip to main content
SpringerLink
Log in

Synthesis of Substituted 1H-Indazoles by Pyrazole Annelation to an Arene

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Substituted 1H-indazoles have been synthesized by reductive intramolecular heterocyclization of 2,4-di-aroyl-N-nitrosomethylanilines and 2,4-diacetyl-N-nitrosomethylaniline. The N-nitrosoanilines were obtained by nitrosation of N-methyl-2,4-diaroyl- and 2,4-diacetylanilines, the products of quaternary 3,5-diaroyl- and 3,5-diacetylpyridinium salt recyclization.

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. C. G. Wermuth, P. Ciapetti, B. Giethlen, and P. Bazzini, Compr. Med. Chem. II, 2, 649 (2006).

    CAS  Google Scholar 

  2. K. Inamoto, M. Katsuno, T. Yoshino, Y. Arai, K. Hiroya, and T. Sakamoto, Tetrahedron, 63, 2695 (2007).

    Article  CAS  Google Scholar 

  3. A. Rahman, S. Malik, H. Cun-heng, and J. Clardy, Tetrahedron Lett., 26, 2759 (1985).

    Article  Google Scholar 

  4. A. Rahman, S. Malik, S. S. Hasan, M. I. Choudhary, C.-Z. Ni, and J. Clardy, Tetrahedron Lett., 36, 1993 (1995).

    Article  Google Scholar 

  5. Y.-M. Liu, J.-S. Yang, and Q.-H. Liu, Chem. Pharm. Bull., 52, 454 (2004).

    Article  CAS  Google Scholar 

  6. A. Schmidt, Adv. Heterocycl. Chem., 85, 67 (2003).

    Article  CAS  Google Scholar 

  7. A. Schmidt, A. Beutler, and B. Snovydovych, Eur. J. Org. Chem., 4073 (2008).

  8. H. Cerecetto, A. Gerpe, M. Gonzalez, V. J. Aran, and C. O. Ocariz, Mini-Rev. Med. Chem., 5, 869 (2005).

    Article  CAS  Google Scholar 

  9. V. J. Aran, C. Ochoa, L. Boiani, P. Buccino, H. Cerecetto, A. Gerpe, M. Gonzalez, D. Montero, J. J. Nogal, A. Gόmez-Barrio, A. Azquetta, A. Lόpez de Cerain, O. E. Piro, and E. E. Castellano, Bioorg. Med. Chem., 13, 3197 (2005).

    Article  CAS  Google Scholar 

  10. J. A. Balfour and S. P. Clissold, Drugs, 39, 575 (1990).

    Article  CAS  Google Scholar 

  11. A. Guglielmotti, A. Cappezzone de Joannon, N. Cazzolla, M. Marchetti, L. Soldo, G. Cavallo, and M. Pinza, Pharmacol. Res., 32, 369 (1995).

    Article  CAS  Google Scholar 

  12. K. M. Hunter, Aust. Dent. J., 23, 164 (1978).

    Article  CAS  Google Scholar 

  13. M. M. Canelas, J. C. Cardoso, M. Gonçalo, and A. Figueiredo, Contact Dermatitis, 63, 85 (2010).

    Article  CAS  Google Scholar 

  14. H. Pelicano, D. S. Martin, R.-H. Xu, and P. Huang, Oncogene, 25, 4633 (2006).

    Article  CAS  Google Scholar 

  15. G. Grassia, M. Maddaluno, A. Guglielmotti, G. Mangano, G. Biondi, P. Maffia, and A. Ialenti, Cardiovasc. Res., 84, 485 (2009).

    Article  CAS  Google Scholar 

  16. M. Bhatia, R. D. Ramnath, L. Chevali, and A. Guglielmotti, Am. J. Physiol. Gastrointest. Liver Physiol., 288, 1259 (2005).

    Article  Google Scholar 

  17. G. L. Plosker and K. L. Goa, Drugs, 42, 805 (1991).

    Article  CAS  Google Scholar 

  18. G. J. Sanger and D. R. Nelson, Eur. J. Pharmacol., 159, 113 (1989).

    Article  CAS  Google Scholar 

  19. http://www.genengnews.com/gen-news-highlights/pfizer-s-phase-iii-trial-in-mrcc-turns-up-positive-results/81244271/

  20. W. Stadlbauer, in: R. Neier (editor), Science of Synthesis: Houben-Weyl Methods of Molecular Transformations, Vol. 12, Georg Thieme Verlag, Stuttgart, New York (2007), p. 227.

    Google Scholar 

  21. B. Cottyn, D. Vichard, F. Terrier, P. Nioche, and C. S. Raman, Synlett, 1203 (2007).

  22. M. Medio-Simόn, M. J. Alvarez de Laviada, and J. Seqúlvada-Arques, J. Chem. Soc., Perkin Trans. 1, 2749 (1990).

  23. A. Díaz-Ortiz, J. R. Carrillo, E. Díez-Barra, A. de la Hoz, M. J. Gόmez-Escalonilla, A. Moreno, and F. Langa, Tetrahedron, 52, 9237 (1996).

    Article  Google Scholar 

  24. S. Matsugo and A. Takamizawa, Synthesis, 852 (1983).

  25. A. Palumbo Piccionello, A. Pace, I. Pibiri, S. Buscemi, and N. Vivona, Tetrahedron, 62, 8792 (2006).

    Article  CAS  Google Scholar 

  26. P. Li, J. Zhao, C. Wu, R. C. Larock, and F. Shi, Org. Lett., 13, 3340 (2011).

    Article  CAS  Google Scholar 

  27. N. A. Markina, A. V. Dubrovskiy, and R. C. Larock, Org. Biomol. Chem., 10, 2409 (2012).

    Article  CAS  Google Scholar 

  28. V. L. M. Silva, A. M. S. Silva, D. C. G. A. Pinto, J. Elguero, and J. A. S. Cavaleiro, Eur. J. Org. Chem., 4468 (2009).

  29. K. Inamoto, M. Katsuno, T. Yoshino, I. Suzuki, K. Hiroya, and T. Sakamoto, Chem. Lett., 33, 1026 (2004).

    Article  CAS  Google Scholar 

  30. Q. Guofu, S. Jiangtao, F. Xichum, W. Lamei, X. Wenjin, and H. Xianming, J. Heterocycl. Chem., 41, 601 (2004).

    Article  Google Scholar 

  31. R. Krishnan, S. A. Lang, Jr, Y. Lin, and R. G. Wilkinson, J. Heterocycl. Chem., 25, 447 (1988).

    Article  CAS  Google Scholar 

  32. K. Uehata, T. Kawakami, and H. Suzuki, J. Chem. Soc., Perkin Trans. 1, 696 (2002).

  33. G. P. Shkil, V. Lusis, D. Muceniece, and R. S. Sagitullin, Tetrahedron, 51, 8599 (1995).

    Article  CAS  Google Scholar 

  34. G. P. Sagitullina, A. K. Garkushenko, N. V. Poendaev, and R. S. Sagitullin, Mendeleev Commun., 22, 167 (2012).

    Article  CAS  Google Scholar 

  35. J. Ozols, R. Dubure, B. Vigante, M. Bundule, I. Zuika, Z. Brūveris, and G. Duburs, Latv. J. Chem., 209 (1991).

  36. A. K. Garkushenko, M. A. Makarova, O. P. Sorokina, N. V. Poendaev, M. A. Vorontsova, and G. P. Sagitullina, Khim. Geterotsikl. Soedin., 586 (2011). [Chem. Heterocycl. Compd., 47, 482 (2011).]

  37. G. W. Cannon and H. L. Whidden, J. Org. Chem., 17, 685 (1952).

    Article  CAS  Google Scholar 

  38. Ya. R. Uldrikis, G. Ya. Dubur, I. V. Dipan, and B. S. Chekavichus, Khim. Geterotsikl. Soedin., 1230 (1975). [Chem. Heterocycl. Compd., 11, 1070 (1975).]

Download references

Author information

Authors and Affiliations

  1. F. M. Dostoevskii Omsk State University, 55a Mira Ave., Omsk, 644077, Russia

    A. K. Garkushenko, O. P. Sorokina, G. A. Kryuchkova, A. A. Zmeev, M. A. Makarova, M. A. Vorontsova & G. P. Sagitullina

Authors
  1. A. K. Garkushenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. O. P. Sorokina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. G. A. Kryuchkova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. A. Zmeev
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. M. A. Makarova
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. M. A. Vorontsova
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. G. P. Sagitullina
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to G. P. Sagitullina.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 297–304.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Garkushenko, A.K., Sorokina, O.P., Kryuchkova, G.A. et al. Synthesis of Substituted 1H-Indazoles by Pyrazole Annelation to an Arene. Chem Heterocycl Comp 49, 273–280 (2013). https://doi.org/10.1007/s10593-013-1244-y

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-013-1244-y

Keywords

Search

Navigation