Skip to main content
SpringerLink
Log in

Synthesis of azachromones and azachromanones

  • REVIEWS
  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

This minireview highlights known methods for the synthesis of azachromones and azachromanones, including the earliest and the latest examples of their synthesis. Methods considered for constructing azachromone or azachromanone system include intramolecular heterocyclization, deprotection–cyclization, spirocyclization, cyclization–aromatization, Ullman-type O-arylation, and C–H activation of pyridine N-oxides.

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. (a) Gaspar, A.; Matos, M. J.; Garrido, J.; Uriarte, E.; Borges, F. Chem. Rev. 2014, 114, 4960. (b) Reis, J.; Gaspar, A.; Milhazes, N.; Borges, F. J. Med. Chem. 2017, 60, 7941. (c) Plaskon, A. S.; Grygorenko, O. O.; Ryabukhin, S. V. Tetrahedron 2012, 68, 2743.

  2. Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893.

    Article  CAS  Google Scholar 

  3. Bell, M. P.; O'dowd, C. R.; Zhang, L.; Tevitt, G. P.; Harrison, T.;Battacharyya, S.; Rountree, J. S. S.; Burkamp, F.; Price, S.; Macleod, C.; Elliott, R. L.; Smith, P.; Blench, T. J.; Dyke, H. J. WO Patent 2011033265A1, 2011.

  4. Friary, R. J.; Schwerdt, J. H.; Ganguly, A. K. US Patent 5034531A, 1991.

  5. Johansson, J. O.; Hansen, H. C.; Chiacchia, F. S.; Wong, N. C. W. WO Patent 2007016525A2, 2007.

  6. Zhmurenko, L. A.; Glozman, O. M.; Zagorevskii, V. A. Chem. Heterocycl. Compd. 1974, 10, 1421. [Khim. Geterotsikl. Soedin. 1974, 1616.]

  7. Glozman, O. M.; Zagorevskii, D. V.; Zhmurenko, L. A.; Zagorevskii, V. A. Chem. Heterocycl. Compd. 1976, 12, 1217. [Khim. Geterotsikl. Soedin. 1976, 1477.]

  8. Khlebnikov, V.; Patel, K.; Zhou, X.; Reddy, M. M.; Su, Zh.; Chiacchia, F. S.; Hansen, H. C. Tetrahedron 2009, 65, 6932.

    Article  CAS  Google Scholar 

  9. Yamazaki, T.; Matoba, K.; Matsuzawa, Y.; Kitagawa, M. Chem. Pharm. Bull. 1977, 25, 1150.

    Article  CAS  Google Scholar 

  10. Harikrishnan, L. S.; Boehm, T. L.; Hollis Showalter, H. D. Synth. Commun. 2001, 31, 519.

    Article  CAS  Google Scholar 

  11. Nakamura, T.; Hara, O.; Tamura, T.; Makino, K.; Hamada, Y. Synlett 2005, 155.

  12. Shen, H. C.; Ding, F.-X.; Wang, S.; Xu, S.; Chen, H.-s.; Tong, X.; Tong, V.; Mitra, K.; Kumar, S.; Zhang, X.; Chen, Yu.; Zhou, G.; Pai, L.-Yu.; Alonso-Garcia, M.; Chen, X.; Zhang, B.; Tata, J. R.; Berger, J. P.; Coletti, S. L. Bioorg. Med. Chem. Lett. 2009, 19, 3398.

    Article  CAS  Google Scholar 

  13. Corbett, J. W.; Freeman-Cook, K. D.; Elliot, R.; Vajdos, F.; Rajamohan, F.; Kohls, D.; Marr, E.; Zhang, H.; Tong, L.; Tu, M.; Murdande, Sh.; Doran, S. D.; Houser, J. A.; Song, W.; Jones, C. J.; Coffey, S. B.; Buzon, L.; Minich, M. L.; Dirico, K. J.; Tapley, S.; McPherson, R. K.; Sugarman, E.; Harwood, H. J., Jr.; Esler, W. Bioorg. Med. Chem. Lett. 2010, 20, 2383.

    Article  CAS  Google Scholar 

  14. Lhommet, G.; Sliwa, H.; Maitte, P. J. Heterocycl. Chem. 1971, 8, 517.

    Article  CAS  Google Scholar 

  15. Cordonnier, G.; Sliwa, H. J. Heterocycl. Chem. 1987, 24, 111.

    Article  CAS  Google Scholar 

  16. Beyett, T. S.; Gan, X.; Reilly, Sh. M.; Gomez, A. V.; Chang, L.; Tesmer, J. J. G.; Salteil, A. R.; Showalter, H. D. Bioorg. Med. Chem. 2018, 26, 5443.

    Article  CAS  Google Scholar 

  17. Bonsall, C.; Hill, J. J. Chem. Soc. C 1967, 1836.

  18. Eiden, F.; Rademacher, G. Arch. Pharm., 1985, 318, 926.

    Article  CAS  Google Scholar 

  19. Sarges, R.; Goldstein, S. W.; Welch, W. M.; Swindell, A. C.; Siegel, T. W.; Beyer, T. A. J. Med. Chem. 1990, 33, 1859.

    Article  CAS  Google Scholar 

  20. Murtiashaw, C. W.; Breitenbach, R.; Goldstein, S. W.; Pezzullo, S. L.; Quallich, G. J.; Sarges, R. J. Org. Chem. 1992, 57, 1930.

    Article  CAS  Google Scholar 

  21. Muthukaman, N.; Tambe, M.; Shaikh, M.; Pisal, D.; Deshmukh, S.; Tondlekar, Sh.; Sarode, N.; Narayana, L.; Gajera, J. M.; Kattige, V. G.; Honnegowda, S.; Karande, V.; Kulkarni, A.; Behera, D.; Jadhav, S. B.; Gudi, C. S.; Khairatkar-Joshi, N.; Gharat, L. A. Bioorg. Med. Chem. Lett. 2017, 27, 2594.

    Article  CAS  Google Scholar 

  22. Lang, R. W.; Wenk, P. F. Helv. Chim. Acta 1988, 71, 596.

    Article  CAS  Google Scholar 

  23. Varnes, J. G.; Marcus, A. P.; Mauger, R. C.; Throner, S. R.; Hoesch, V.; King, M. M.; Wang, X.; Sygowski, L. A.; Spear, N.; Gadient, R.; Brown, D. G.; Campbell, J. B. Bioorg. Med. Chem. Lett. 2011, 21, 1402.

    Article  CAS  Google Scholar 

  24. Madsen-Duggan, C. B.; Debenham, J. S.; Walsh, T. F.; Yan, L.; Huo, P.; Wang, J.; Tong, X.; Lao, J.; Fong, T. M.; Xiao, J. Ch.; Huang, C. R.-R. C.; Shen, Ch.-P.; Stribling, D. S.; Shearman, L. P.; Strack, A. M.; Goulet, M. T.; Hale, J. J. Bioorg. Med. Chem. Lett. 2010, 20, 3750.

    Article  CAS  Google Scholar 

  25. Yan, L.; Huo, P.; Debenham, J. S.; Madsen-Duggan, C. B.; Lao, J.; Chen, R. Z.; Xiao, J. Ch.; Shen, Ch.-P.; Stribling, D. S.; Shearman, L. P.; Strack, A. M.; Tsou, N.; Ball, R. G.; Wang, J.; Tong, X.; Bateman, T. J.; Reddy, V. B. G.; Fong, T. M.; Hale, J. J. J. Med. Chem. 2010, 53, 4028.

    Article  CAS  Google Scholar 

  26. Sosnovskikh, V. Ya. In Fluorine in Heterocyclic Chemistry; Nenajdenko, V., Ed.; Springer International Publishing, 2014, Vol. 2, p. 211.

  27. Sosnovskikh, V. Ya.; Barabanov, M. A. J. Fluorine Chem. 2003, 120, 25.

    Article  CAS  Google Scholar 

  28. Sosnovskikh, V. Ya.; Irgashev, R. A.; Barabanov, M. A. Synthesis 2006, 2707.

  29. Safrygin, A. V.; Barabanov, M. A.; Irgashev, R. A.; Sosnovskikh, V. Ya. Chem. Heterocycl. Compd. 2015, 51, 838. [Khim. Geterotsikl. Soedin. 2015, 51, 838.]

  30. Sosnovskikh, V. Ya.; Barabanov, M. A.; Usachev, B. I. J. Org. Chem. 2004, 69, 8297.

    Article  CAS  Google Scholar 

  31. Sosnovskikh, V. Ya.; Usachev, B. I.; Sevenard, D. V.; Röschenthaler, G.-V. J. Fluorine Chem. 2005, 126, 779.

    Article  CAS  Google Scholar 

  32. Sosnovskikh, V. Ya.; Barabanov, M. A.; Usachev, B. I. Russ. Chem. Bull., Int. Ed. 2003, 52, 1758. [Izv. Akad. Nauk, Ser. Khim. 2003, 1668.]

  33. Zhao, J; Zhao, Y.; Fu, H. Angew. Chem., Int. Ed. 2011, 50, 3769.

  34. Wang, D.; Feng, H.; Li, L.; Liu, Z.; Yan, Z.; Yu, P. J. Org. Chem. 2017, 82, 11275.

    Article  CAS  Google Scholar 

  35. Gan, X.; Showalter, H. D. Tetrahedron Lett. 2019, 60, 2035

    Article  CAS  Google Scholar 

Download references

Funding

This work was funded by Ministry of Education and Science of Ukraine (grant No. 19БФ037-03).

Author information

Authors and Affiliations

  1. Taras Shevchenko National University of Kyiv, 60 Volodymyrska St, Kyiv, 01601, Ukraine

    Yehor S. Malets, Viktoriia S. Moskvina & Oleksandr O. Grygorenko

  2. Enamine Ltd., 78 Chervonotkatska St, Kyiv, 02094, Ukraine

    Yehor S. Malets & Oleksandr O. Grygorenko

  3. V. P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Science of Ukraine, 1 Murmanska St, Kyiv, 02094, Ukraine

    Yehor S. Malets, Viktoriia S. Moskvina & Volodymyr S. Brovarets

Authors
  1. Yehor S. Malets
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Viktoriia S. Moskvina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Oleksandr O. Grygorenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Volodymyr S. Brovarets
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Viktoriia S. Moskvina.

Additional information

Dedicated to Prof. Dr. V. P. Khilya on the occasion of his 80th birthday

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(11), 1007–1012

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Malets, Y.S., Moskvina, V.S., Grygorenko, O.O. et al. Synthesis of azachromones and azachromanones. Chem Heterocycl Comp 55, 1007–1012 (2019). https://doi.org/10.1007/s10593-019-02570-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-019-02570-x

Keywords

Search

Navigation