Synthesis of aromatic bishydrazones: new facets of a known reaction

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

Abstract

This work reconsiders the known condensation reaction of 1,2-diketones with arylhydrazines in the synthesis of the corresponding bishydrazones. It was shown that the reaction outcome significantly depends on the nature of the substituent of the aromatic ring of arylhydrazine. In addition, representatives of unsymmetrically substituted bishydrazones, rarely found in the literature, were obtained. The proposed approach is easy to carry out and isolate target bishydrazones, which opens the way to the preparation of various nitrogen-containing molecular systems based on them.

About the authors

M. A. Epishina

N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

A. S. Kulikov

N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

L. L. Fershtat

N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Email: fershtat@ioc.ac.ru

References

  1. Popiolek L. // Med. Chem. Res. 2017. Vol. 26. P. 287. doi: 10.1007/s00044-016-1756-y
  2. Popiolek L. // Biomed. Pharmacother. 2023. Vol. 163. P. 114853. doi: 10.1016/j.biopha.2023.114853
  3. K�lmel D.K., Kool E.T. // Chem. Rev. 2017. Vol. 117. P. 10358. doi: 10.1021/acs.chemrev.7b00090
  4. Bystrov D.M., Ananyev I.V., Fershtat L.L., Makhova N.N. // J. Org. Chem. 2020. Vol. 85. P. 15466. doi: 10.1021/acs.joc.0c02243
  5. Kulikov A.S., Epishina M.A., Churakov A.I., Anikina L.V., Fershtat L.L., Makhova N.N. // Mendeleev Commun. 2018. Vol. 28. P. 623. doi: 10.1016/j.mencom.2018.11.020
  6. Butler R.N., Cunningham D., McArdle P., O'Halloran G.A. // J. Chem. Soc. Chem. Commun. 1988. Vol. 3. P. 232. doi: 10.1039/C39880000232
  7. Butler R.N., Evans A.M., McNeela E.M., O'Halloran G.A., O'Shea P.D., Cunningham D., McArdle P. // J. Chem. Soc. Perkin Trans. 1 1990. P. 2527. doi: 10.1039/P19900002527
  8. Wu Z.-C., Boger D.L. // J. Am. Chem. Soc. 2019. Vol. 141. P. 16388. doi: 10.1021/jacs.9b07744
  9. Wu Z.-C., Boger D.L. // J. Org. Chem. 2022. Vol. 87. P. 16829. doi: 10.1021/acs.joc.2c02687
  10. Japp F.R., Klingemann F. // Lieb. Ann. Chem. 1888. Vol. 247. P. 190. doi: 10.1002/jlac.18882470208
  11. Butler R.N., O'Shea D.F. // Heterocycles. 1994. Vol. 37. P. 571. doi: 10.3987/REV-93-SR1
  12. Tabbiche A., Bouchama A., Chafai N., Zaidi F., Chiter C., Yahiaoui M., Abiza A. // J. Mol. Struct. 2022. Vol. 1261. P. 132865. doi: 10.1016/j.molstruc.2022.132865
  13. Butler R.N., Hanniffy J.M., Stephens J.C., Burke L.A. // J. Org. Chem. 2008. Vol. 73. P. 1354. doi: 10.1021/jo702423z
  14. Nagaraj K., Singh A., Shetty A.N., Trivedi D.R. // Supramol. Chem. 2021. Vol. 33. P. 534. doi: 10.1080/10610278.2022.2087524

Copyright (c) 2023 Russian Academy of Sciences

This website uses cookies

You consent to our cookies if you continue to use our website.

About Cookies