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Novel structural type of bridged urea derivatives bearing azatricyclo[4.3.1.03,8]decane moiety

  • Alexander A. Alexeev
  • Evgeniya V. NurievaEmail author
  • Konstantin A. Lyssenko
  • Yuri K. Grishin
  • Olga N. Zefirova
Original Research

Abstract

In an attempt to synthesize 4-thia-6-azatricyclo[5.3.1.13,9]dodecan-5-imine as putative antihypotensive agent with prolonged effect, a reaction of 1-[(1RS,3SR,5SR)-bicyclo[3.3.1]non-6-en-3-yl]-3-tert-butylthiourea in the presence of bromine was undertaken. The intramolecular cyclization however was accompanied by precursive oxidation of thiourea to urea fragment and proceeded via nitrogen atom yielding the bridged tricyclic urea derivative as determined by X-ray analysis and liquid chromatography–mass spectrometry technique. The compounds obtained in the present study belong to a novel and unusual structural type of bridged tricyclic ureas.

Keywords

Bridged tricyclic ureas Intramolecular cyclization Oxidation of thiourea 

Notes

Acknowledgments

The authors are grateful to the Center for molecular composition studies of INEOS RAS, where X-ray diffraction data were collected.

Funding information

This work was financially supported by Russian Fund of Fundamental Research (project no. №18-03-00524). Part of the work was made within the State assignment for the Department of Medicinal Chemistry and Advanced Organic Synthesis of MSU. The spectral data were recorded on the equipment purchased at the expense of M.V. Lomonosov Moscow State University Program of Development.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Alexander A. Alexeev
    • 1
  • Evgeniya V. Nurieva
    • 1
    Email author
  • Konstantin A. Lyssenko
    • 1
    • 2
  • Yuri K. Grishin
    • 1
  • Olga N. Zefirova
    • 1
    • 3
  1. 1.Department of ChemistryLomonosov Moscow State UniversityMoscowRussian Federation
  2. 2.Institute of Organoelement Compounds of Russian Academy of SciencesMoscowRussian Federation
  3. 3.Institute of Physiologically Active CompoundsRussian Academy of SciencesMoscow RegionRussian Federation

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