Chemistry of Natural Compounds

, Volume 55, Issue 4, pp 692–695 | Cite as

Synthesis of a 1,2,3-Thiadiazole of Butyl Glycyrrhetinate

  • L. A. BaltinaEmail author
  • D. M. Shayakhmetova
  • L. A. BaltinaJr.
  • T. R. Nugumanov

The butyl ester of 3-oxoglycyrrhetinic acid reacted with semicarbazide in EtOH in the presence of NaOAc to produce the 3-semicarbazone, Hurd–Mori cyclization of which gave in 85% yield a 1,2,3-thiadiazole annelated to ring A.


triterpenoids glycyrrhetinic acid semicarbazone thiadiazole 



The work was financially supported by Grant RFBR-MNT_a 18-53-52004 using equipment at the Khimiya CUC, UfIC, UFRC, RAS.


  1. 1.
    H. Sheng and H. Sun, Nat. Prod. Rep., 28, 543 (2011).CrossRefPubMedGoogle Scholar
  2. 2.
    R. Paduch and M. Kandefer-Szerszen, Mini-Rev. Org. Chem., 11, 262 (2014).CrossRefGoogle Scholar
  3. 3.
    J. A. Salvador, A. S. Leal, D. P. S.Alho, B. M. F.Goncalves, A. S. Valdeira, and V. I. S. Mendes, Stud. Nat. Prod. Chem., 41, 33 (2014).CrossRefGoogle Scholar
  4. 4.
    G. A. Tolstikov, L. A. Baltina, V. P. Grankina, R. M. Kondratenko, and T. G. Tolstikova, Licorice: Biodiversity, Chemistry, Medical Applications [in Russian], Akademicheskoe Izd. Geo, Novosibirsk, 2007, 311 pp.Google Scholar
  5. 5.
    C. S. Graebin, H. Verli, and J. A. Guimaraes, J. Braz. Chem. Soc., 21, 1595 (2010).CrossRefGoogle Scholar
  6. 6.
    A. Roohbakhsh, M. Iranshahy, and M. Iranshahi, Curr. Med. Chem., 23, 498 (2016).CrossRefPubMedGoogle Scholar
  7. 7.
    B. Xu, G.-R. Wu, X.-Y. Zhang, M.-M. Yan, R. Zhao, N.-N. Xue, K. Fang, H. Wang, M. Chen, W.-B. Guo, P.-L. Wang, and H.-M. Lei, Molecules, 22, 924 (2017).CrossRefPubMedCentralGoogle Scholar
  8. 8.
    M. Kvasnica, M. Urban, N. J. Dickinson, and J. Sarek, Nat. Prod. Rep., 32, 1303 (2015).CrossRefPubMedGoogle Scholar
  9. 9.
    L. A. Baltina, Jr., M. V. Khudobko, L. R. Mikhailova, L. A. Baltina, V. A. Fedorova, Ya. A. Orshanskaya, V. V. Zarubaev, and O. I. Kiselev, Chem. Nat. Compd., 50, 473 (2014).CrossRefGoogle Scholar
  10. 10.
    C. Gao, F.-J. Dai, H.-W. Cui, Sh.-H. Peng, Y. He, X. Wang, Zh.-F. Yi, and W.-W. Qiu, Chem. Biol. Drug Des., 84, 223 (2014).CrossRefPubMedGoogle Scholar
  11. 11.
    A. J. Gordon and R. A. Ford, The Chemist’s Companion, Wiley-Interscience, New York, 1972.Google Scholar
  12. 12.
    L. A. Baltina, O. B. Flekhter, Zh. M. Putieva, R. M. Kondratenko, L. V. Krasnova, and G. A. Tolstikov, Khim.-farm. Zh., 30, No. 4, 47 (1996).Google Scholar

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© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • L. A. Baltina
    • 1
    Email author
  • D. M. Shayakhmetova
    • 2
  • L. A. BaltinaJr.
    • 1
  • T. R. Nugumanov
    • 1
  1. 1.Ufa Institute of Chemistry, Subdivision of Ufa Federal Research CentreRussian Academy of SciencesUfaRussian Federation
  2. 2.Bashkir State UniversityUfaRussian Federation

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