Skip to main content
SpringerLink
Log in

Efficient method for the synthesis of 1,3-unsubstituted 2-imino-5-oxooctahydroimidazo[4,5-d]imidazolium iodides based on thioglycolurils

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

A facile and efficient two-step synthetic route to previously inaccessible 1,3-unsubstituted 2-imino-5-oxooctahydroimidazo[4,5-d]-imidazol-1-ium iodides has been developed using easily accessible thioglycolurils, MeI, and various primary amines, morpholine, or ethylene diamine. The structure of representative products and hydrogen-bonding pattern in their crystals have been investigated by X-ray diffraction.

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

Figure 1.

Similar content being viewed by others

References

  1. Luengo, J. I.; Chan, J. A.; Breen, A. L. US Patent 5981551.

  2. Luengo, J. I.; Duffy, K. J. US Patent 6630470.

  3. Sal'keeva, L. K.; Röschenthaler, G.-V.; Bakibaev, A. A.; Voitiček, P.; Shibaeva, A. K.; Taishibekova, E. K.; Zhortarova, A. A.; Sugralina, L. M. Russ. J. Gen. Chem. 2015, 85, 88. [Zh. Obshch. Khim. 2015, 85, 95.]

    Article  CAS  Google Scholar 

  4. Wild, U.; Kaifer, E.; Himmel, H.-J. Eur. J. Inorg. Chem. 2011, 4220.

  5. Kony, M.; Dagley, I. J.; Leslie, D. R. J. Org. Chem. 1994, 59, 5623.

    Article  CAS  Google Scholar 

  6. Ramakrishnan, V. T.; Vedachalam, M.; Boyer, J. H. J. Heterocycl. Chem. 1991, 2, 669.

    CAS  Google Scholar 

  7. (a) Singh, M.; Solel, E.; Keinan, E.; Reany, O. Chem.–Eur. J. 2016, 22, 8848. (b) Gieling, G. T. W.; Scheeren, H. W.; Israel, R.; Nolte, R. J. M. Chem. Commun. 1996, 241. (c) Solel, E.; Singh, M.; Reany, O.; Keinan, E. Phys. Chem. Chem. Phys. 2016, 18, 13180.

  8. Tsuchiya, Sh.; Cho, Yu.; Konoki, K.; Nagasawa, K.; Oshima, Ya.; Yotsu-Yamashita, M. Chem.–Eur. J. 2015, 21, 7835.

    Article  CAS  PubMed  Google Scholar 

  9. Maas, G.; Brückmann, R.; Feith, B. J. Heterocycl. Chem. 1985, 22, 907.

    Article  CAS  Google Scholar 

  10. Kravchenko, A. N.; Baranov, V. V.; Gazieva, G. A. Russ. Chem. Rev. 2018, 87, 89. [Usp. Khim. 2018, 87, 89.]

    CAS  Google Scholar 

  11. (a) Gazieva, G. A.; Anikina, L. V.; Nechaeva, T. V.; Pukhov, S. A.; Karpova, T. B.; Popkov, S. V.; Nelyubina, Yu. V.; Kolotyrkina, N. G.; Kravchenko, A. N. Eur. J. Med. Chem. 2017, 140, 141. (b) Gazieva, G. A.; Nechaeva, T. V.; Kostikova, N. N.; Sigay, N. V.; Serkov, S. A.; Popkov, N. N. Russ. Chem. Bull., Int. Ed. 2018, 67, 1059. [Izv. Akad Nauk, Ser. Khim. 2018, 67, 1059.]

  12. Aoyagi, N.; Endo, T. Synth. Commun. 2017, 47, 442.

    Article  CAS  Google Scholar 

  13. Aspinall, S. R.; Bianco, E. J. J. Am. Chem. Soc. 1951, 73, 602.

    Article  CAS  Google Scholar 

  14. Baranov, V. V.; Nelyubina, Yu. V.; Kravchenko, A. N.; Kolotyrkina, N. G.; Biriukova, K. A. Tetrahedron Lett. 2015, 56, 6085.

    Article  CAS  Google Scholar 

  15. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, A64, 112.

    Article  CAS  Google Scholar 

Download references

This work was supported by the Russian Science Foundation (project 17-73-10415).

The X-ray diffraction data have been collected at the Center for Molecular composition studies of A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences.

Author information

Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow, 119991, Russia

    Vladimir V. Baranov, Evgeniya L. Yatsenko & Angelina N. Kravchenko

  2. D. I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Sq., Moscow, 125047, Russia

    Evgeniya L. Yatsenko

  3. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St., Moscow, 119991, Russia

    Elizaveta K. Melnikova & Yulia V. Nelyubina

  4. M. V. Lomonosov Moscow State University, 1-3 Leninskie Gory, Moscow, 119991, Russia

    Elizaveta K. Melnikova

Authors
  1. Vladimir V. Baranov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Evgeniya L. Yatsenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Elizaveta K. Melnikova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yulia V. Nelyubina
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Angelina N. Kravchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Vladimir V. Baranov.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(2), 160–166

Electronic supplementary material

ESM 1

(PDF 2423 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Baranov, V.V., Yatsenko, E.L., Melnikova, E.K. et al. Efficient method for the synthesis of 1,3-unsubstituted 2-imino-5-oxooctahydroimidazo[4,5-d]imidazolium iodides based on thioglycolurils. Chem Heterocycl Comp 55, 160–166 (2019). https://doi.org/10.1007/s10593-019-02433-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-019-02433-5

Keywords

Search

Navigation