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Glycolurils in α-ureido- and α-aminoalkylation Reactions. 3**. N-(hydroxymethyl)glycolurils in Reactions with Aliphatic Amines and Amino Acids*

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Chemistry of Heterocyclic Compounds Aims and scope

The condensation of aliphatic alkylamines and achiral amino acids with 1,5-butano-2,4,6,8-tetra-(hydroxymethyl)- and 2,4,6,8-tetra(hydroxymethyl)glycolurils was used to prepare and characterize polycyclic condensed compounds (including some previously unknown examples) containing glycoluril and alkylamine fragments. X-ray structural study of the obtained compounds was used to identify n(N)→σ(C–H) anomeric interaction.

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Notes

  1. The patented Markush formula and Markush structures are described in detail by Е. А. Ustinov, O. V. Chelyshev "Regarding broad (generic) formulae of chemical compounds in worldwide and Russian patents" [in Russian] (Pat. inf., Issue 3, 45 (1995)). A Markush formula by itself does not denote any particular compound, but rather serves as a convenient depiction of generalized chemical structures.

  2. Potassium salts were prepared by adding KOH (0.1 mol) to a solution of the corresponding acid or dipeptide in water (6 ml).

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The work was performed with support from the Program of Department of Chemistry and Material Sciences of the Russian Academy of Sciences (OKh-9).

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Authors and Affiliations

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

    A. N. Kravchenko, I. E. Chikunov & V. V. Baranov

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 2 Vavilova St., Moscow, 119991, Russia

    K. A. Lyssenko

Authors
  1. A. N. Kravchenko
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  2. I. E. Chikunov
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  3. K. A. Lyssenko
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  4. V. V. Baranov
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Correspondence to A. N. Kravchenko.

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* Dedicated to Academician of the Russian Academy of Sciences Yu. N. Bubnov on the occasion of his 80th birthday.

**For Communication 2, see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1434-1444, September, 2014.

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Kravchenko, A.N., Chikunov, I.E., Lyssenko, K.A. et al. Glycolurils in α-ureido- and α-aminoalkylation Reactions. 3**. N-(hydroxymethyl)glycolurils in Reactions with Aliphatic Amines and Amino Acids*. Chem Heterocycl Comp 50, 1322–1331 (2014). https://doi.org/10.1007/s10593-014-1595-z

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