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Russian Chemical Bulletin

, Volume 54, Issue 3, pp 691–704 | Cite as

Synthesis of new chiral mono-, di-, tri-, and tetraalkylglycolurils

  • A. N. Kravchenko
  • A. S. Sigachev
  • E. Yu. Maksareva
  • G. A. Gazieva
  • N. S. Trunova
  • B. V. Lozhkin
  • T. S. Pivina
  • M. M. Il’in
  • K. A. Lyssenko
  • Yu. V. Nelyubina
  • V. A. Davankov
  • O. V. Lebedev
  • N. N. Makhova
  • V. A. Tartakovsky
Article

Abstract

Two general procedures were developed for the synthesis of chiral N-mono-, N, N′-di-, N, NN″-tri-, and N, N′, N″, N′″-tetraalkylglycolurils based on the reactions of 4,5-dihydroxy-imidazolidin-2-ones or glyoxal with one or two moles of alkylureas, respectively, by acid catalysis. The reactions of N-monoalkyl- and N, N′-dialkylureas with glyoxal proceed regioselectively. The mechanism of these reactions was suggested and partly confirmed by quantum-chemical calculations and experimental data. The enantiomeric separation of some chiral glycolurils by chiral-phase HPLC was carried out for the first time.

Key words

glycolurils chirality 4,5-dihydroxyimidazolidin-2-ones mono- and dialkyl-ureas quantum-chemical calculations enantiomeric analysis and separation regioselectivity 

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Copyright information

© Springer Science+Business Media, Inc. 2005

Authors and Affiliations

  • A. N. Kravchenko
    • 1
  • A. S. Sigachev
    • 1
  • E. Yu. Maksareva
    • 1
  • G. A. Gazieva
    • 1
  • N. S. Trunova
    • 1
  • B. V. Lozhkin
    • 1
  • T. S. Pivina
    • 1
  • M. M. Il’in
    • 2
  • K. A. Lyssenko
    • 2
  • Yu. V. Nelyubina
    • 2
  • V. A. Davankov
    • 2
  • O. V. Lebedev
    • 1
  • N. N. Makhova
    • 1
  • V. A. Tartakovsky
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation
  2. 2.A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussian Federation

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