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Chemistry of Heterocyclic Compounds

, Volume 55, Issue 2, pp 160–166 | Cite as

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

  • Vladimir V. BaranovEmail author
  • Evgeniya L. Yatsenko
  • Elizaveta K. Melnikova
  • Yulia V. Nelyubina
  • Angelina N. Kravchenko
Article
  • 29 Downloads

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.

Keywords

iminoglycolurils isothiouronium salts thioglycolurils condensation S-methylation 

Notes

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.

Supplementary material

10593_2019_2433_MOESM1_ESM.pdf (2.4 mb)
ESM 1 (PDF 2423 kb)

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Copyright information

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

Authors and Affiliations

  • Vladimir V. Baranov
    • 1
    Email author
  • Evgeniya L. Yatsenko
    • 1
    • 2
  • Elizaveta K. Melnikova
    • 3
    • 4
  • Yulia V. Nelyubina
    • 3
  • Angelina N. Kravchenko
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussia
  2. 2.D. I. Mendeleev University of Chemical Technology of RussiaMoscowRussia
  3. 3.A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussia
  4. 4.M. V. Lomonosov Moscow State UniversityMoscowRussia

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