Skip to main content
SpringerLink
Log in

Convenient synthesis of imidazo[1,5-a]pyrimidine derivatives and their unusual recyclization into 3H-imidazo[4,5-b]pyridine derivatives

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

New derivatives of imidazo[1,5-a]pyrimidine have been synthesized by cyclization of in situ generated 1H-imidazol-4(5)-amine with 1,3-diketones or malondialdehyde derivatives. Utilization of asymmetrical 1,3-diketones leads to the formation of a mixture of regioisomers. The discovered conversion of imidazo[1,5-a]pyrimidine core into 3H-imidazo[4,5-b]pyridine that takes place only under acidic conditions can be considered as a new version of Dimroth rearrangement involving cleavage of C–N bond and formation of C–C bond.

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. Tully, W. R.; Gardner, C. R.; Gillespie, R. J.; Westwood, R. J. Med. Chem. 1991, 34, 2060.

    Article  CAS  Google Scholar 

  2. Rupert, K. C.; Henry, J. R.; Dodd, J. H.; Wadsworth, S. A.; Cavender, D. E.; Olini, G. C.; Fahmy, B.; Siekierka, J. J. Bioorg. Med. Chem. Lett. 2003, 10, 347.

    Article  Google Scholar 

  3. Abdel-Mohsen, H. T.; Abood, A.; Flanagan, K. J.; Meindl, A.; Senge, M. O.; El-Diwani, H. I. Arch. Pharm. 2020, 353, 1.

    Google Scholar 

  4. Lythgoe, D. J.; Ramsden, C. A. Adv. Heterocycl. Chem. 1994, 61, 1.

    Article  CAS  Google Scholar 

  5. (a) Zhang, Z.; Zhang, P.; Kang, T.; Zhu, M. Chin. J. Chem. 2012, 30, 997. (b) Hannah, D. R.; Stevens, M. F. G. J. Chem. Res., Synop. 2003, 398. (c) Moehrle, H.; Wirtz, M. Pharmazie 1999, 54, 115. (d) Chern, J. W.; Lee, C. C.; Liaw, Y. C.; Wang, A. H. J. Heterocycles 1992, 34, 1133. (e) Novinson, T.; O'Brien, D. E.; Robins, R. K. J. Heterocycl. Chem. 1974, 11, 873.

  6. (a) Wendt, M. D.; Kunzer, A.; Henry, R. F.; Cross, J.; Pagano, T. G. Tetrahedron Lett. 2007, 48, 6360. (b) Campos, J. F.; Loubidi, M.; Scherrmann, M.-C.; Berteina-Raboin, S. Molecules 2018, 23, 684.

  7. (a) Wu, J.; Xing, X.; Cuny, G. D. Lett. Org. Chem. 2009, 6, 203. (b) Follmann, M.; Ackerstaff, J.; Redlich, G.; Wunder, F.; Lang, D.; Kern, A.; Fey, P.; Griebenow, N.; Kroh, W.; Becker-Pelster, E.-M.; Kretschmer, A.; Geiss, V.; Li, V.; Straub, A.; Mittendorf, J.; Jautelat, R.; Schirok, H.; Schlemmer, K.-H.; Lustig, K.; Gerisch, M.; Knorr, A.; Tinel, H.; Mondritzki, T.; Trübel, H.; Sandner, P.; Stasch, J.-P. J. Med. Chem. 2017, 60, 5146.

  8. Elkholy, Y. M.; Erian, A. W. Heteroat. Chem. 2003, 14, 503.

    Article  CAS  Google Scholar 

  9. (a) Guerret, P.; Janquier, R; Maury, G. Bull. Soc. Chim. Fr. 1972, 2481. (b) Al-Shaar, A. H. M.; Chambers, R. K.; Gilmour, D. W.; Lythgoe, D. J.; McClenaghan, I.; Ramsden, C. A. J. Chem. Soc., Perkin Trans. 1 1992, 2789.

  10. Ramsden, C. A. Chem. Heterocycl. Compd. 1995, 31, 1155. [Khim. Geterotsikl. Soedin. 1995, 1323.]

  11. Al-Shaar, A. H. M.; Adnan, H. M.; Gilmour, D. W.; Lythgoe, D. J.; McClenaghan, I.; Ramsden, C. A. J. Chem. Soc., Perkin Trans. 1 1992, 2779.

  12. Magee, W. L.; Rao, C. B.; Glinka, J.; Hui, H.; Amick, T. J.; Fiscus, D.; Kakodkar, S.; Nair, M.; Shechter, H. J. Org. Chem. 1987, 52, 5538.

    Article  CAS  Google Scholar 

  13. Nolte, B.; Suc-Holeiki, I.; Feuerstein, T.; Gallagher, B. M., Jr.; Wu, X.; Steeneck, C.; Gege, C.; Deng, H.; Van Veldhuizen, J.; Taveras, A. WO Patent 2008063671.

  14. Nolsoe, J. M. J.; Ertan, A.; Svensson, M.; Weigelt, D. J. Heterocycl. Chem. 2010, 47, 878.

    Article  Google Scholar 

  15. Balaban, I. E. J. Chem. Soc. 1930, 268.

  16. Baladi, T.; Granzhan, A.; Piguel, S. Eur. J. Org. Chem. 2016, 2421.

  17. Stanovnik, B.; Tišler, M. Synthesis 1974, 120.

Download references

Author information

Authors and Affiliations

  1. L. M. Litvinenko Institute of Physical-Organic Chemistry and Coal Chemistry, 50 Kharkivs’ke shose, Kyiv, 02160, Ukraine

    Valery S. Tolkunov, Andrew S. Tolkunov, Olga V. Smirnova & Sergei V. Tolkunov

Authors
  1. Valery S. Tolkunov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Andrew S. Tolkunov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Olga V. Smirnova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Sergei V. Tolkunov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Valery S. Tolkunov.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(5), 554–559

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Tolkunov, V.S., Tolkunov, A.S., Smirnova, O.V. et al. Convenient synthesis of imidazo[1,5-a]pyrimidine derivatives and their unusual recyclization into 3H-imidazo[4,5-b]pyridine derivatives. Chem Heterocycl Comp 57, 554–559 (2021). https://doi.org/10.1007/s10593-021-02942-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-021-02942-2

Keywords

Search

Navigation