Home / Publications / Chiral glycouril, 2,6-diethyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione: spontaneous resolution, reactivity and absolute configuration

Chiral glycouril, 2,6-diethyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione: spontaneous resolution, reactivity and absolute configuration

Remir Grigorevich Kostyanovsky 1
Remir Grigorevich Kostyanovsky
, 
Konstantin Alexandrovich Lyssenko 2
Konstantin Alexandrovich Lyssenko
, 
Gulnara Konstantinovna Kadorkina 1
Gulnara Konstantinovna Kadorkina
, 
Oleg Vasilevich Lebedev 3
Oleg Vasilevich Lebedev
, 
Angelina Nikolaevna Kravchenko 3
Angelina Nikolaevna Kravchenko
, 
Ivan Ivanovich Chervin 1
Ivan Ivanovich Chervin
, 
Vasily Remirovich Kostyanovsky 1
Vasily Remirovich Kostyanovsky
10.1070/MC1998v008n06ABEH001035
Published 1998-12-16
Communication , Volume 8, Issue 6, 231-233
27
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Kostyanovsky R. G. et al. Chiral glycouril, 2,6-diethyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione: spontaneous resolution, reactivity and absolute configuration // Mendeleev Communications. 1998. Vol. 8. No. 6. pp. 231-233.
GOST all authors (up to 50) Copy
Kostyanovsky R. G., Lyssenko K. A., Kadorkina G. K., Lebedev O. V., Kravchenko A. N., Chervin I. I., Kostyanovsky V. R. Chiral glycouril, 2,6-diethyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione: spontaneous resolution, reactivity and absolute configuration // Mendeleev Communications. 1998. Vol. 8. No. 6. pp. 231-233.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1070/MC1998v008n06ABEH001035
UR - https://mendcomm.colab.ws/publications/10.1070/MC1998v008n06ABEH001035
TI - Chiral glycouril, 2,6-diethyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione: spontaneous resolution, reactivity and absolute configuration
T2 - Mendeleev Communications
AU - Kostyanovsky, Remir Grigorevich
AU - Lyssenko, Konstantin Alexandrovich
AU - Kadorkina, Gulnara Konstantinovna
AU - Lebedev, Oleg Vasilevich
AU - Kravchenko, Angelina Nikolaevna
AU - Chervin, Ivan Ivanovich
AU - Kostyanovsky, Vasily Remirovich
PY - 1998
DA - 1998/12/16
PB - Mendeleev Communications
SP - 231-233
IS - 6
VL - 8
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{1998_Kostyanovsky,
author = {Remir Grigorevich Kostyanovsky and Konstantin Alexandrovich Lyssenko and Gulnara Konstantinovna Kadorkina and Oleg Vasilevich Lebedev and Angelina Nikolaevna Kravchenko and Ivan Ivanovich Chervin and Vasily Remirovich Kostyanovsky},
title = {Chiral glycouril, 2,6-diethyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione: spontaneous resolution, reactivity and absolute configuration},
journal = {Mendeleev Communications},
year = {1998},
volume = {8},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1070/MC1998v008n06ABEH001035},
number = {6},
pages = {231--233},
doi = {10.1070/MC1998v008n06ABEH001035}
}
MLA
Cite this
MLA Copy
Kostyanovsky, Remir Grigorevich, et al. “Chiral glycouril, 2,6-diethyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione: spontaneous resolution, reactivity and absolute configuration.” Mendeleev Communications, vol. 8, no. 6, Dec. 1998, pp. 231-233. https://mendcomm.colab.ws/publications/10.1070/MC1998v008n06ABEH001035.

Abstract

The title glycouril 1 was spontaneously resolved into enantiomers by crystallisation from H2O and sorting of conglomerate crystals, then N-chlorination and N-aminomethylation to give 2, 3 and 4, respectively, were studied. The absolute configuration 1R,5R-(+) was determined by an X-ray diffraction study of diastereomeric N,N-bis-aminomethyl derivative (−)-4.

References

1.
Chirality directed self-assembly. Resolution of 2,5-diazabicyclo[2.2.2]octane-3,6-dione and crystal structures of its racemic and (−) enantiomeric forms
Brienne M., Gabard J., Leclercq M., Lehn J., Cesario M., Pascard C., Chevé M., Dutruc-Rosset G.
Tetrahedron Letters, 1994
2.
Kostyanovsky R.G., El’natanov Y.I., Krutius O.N., Chervin I.I., Lyssenko K.A.
Mendeleev Communications, 1998
3.
10.1070/MC1998v008n06ABEH001035_bib3
Tsintsadze
Soobshcheniya AN GSSR, 1986
4.
10.1070/MC1998v008n06ABEH001035_bib4
Shamuratov
Khim. Geterotsikl. Soedin., 1991
5.
10.1070/MC1998v008n06ABEH001035_bib5
Rybakov
Zh. Strukt. Khim., 1989
7.
10.1070/MC1998v008n06ABEH001035_bib7
Boyle
Proc. Roy. Irish Acad., 1983
8.
Methods of synthesis of nitrogen-containing heterocycles using ureas and related compounds
Bakibaev A.A., Yagovkin A.Y., Vostretsov S.N.
Russian Chemical Reviews, 1998
9.
10.1070/MC1998v008n06ABEH001035_bib9
Lebedev
Tselenapravlennyi Poisk Novykh Neirotropnykh Preparatovnl, 1983
10.
CHIRAL DRUGS
STINSON S.C.
Chemical & Engineering News, 1992
11.
CHIRAL DRUGS
STINSON S.C.
Chemical & Engineering News, 1995
12.
10.1070/MC1998v008n06ABEH001035_bib10_3
Stinson
Chem. Eng. News, 1997
13.
2,4,6,8-Tetraazabarbaralanes: Models for tetraazasemibullvalenes
Gompper R., Nöth H., Spes P.
Tetrahedron Letters, 1988
14.
Self-Assembling Capsules
Conn M.M., Rebek J.
Chemical Reviews, 1997
15.
Chemical Selection and Self‐Assembly in a Cyclization Reaction
Rudkevich D.M., Rebek J.
Angewandte Chemie International Edition in English, 1997
17.
Chiral Capsules. 1. Softballs with Asymmetric Surfaces Bind Camphor Derivatives
Tokunaga Y., Rebek J.
Journal of the American Chemical Society, 1998
18.
Structural Rules Governing Self-Assembly Emerge from New Molecular Capsules
Rivera J.M., Martín T., Rebek J.
Journal of the American Chemical Society, 1998
19.
Synthesis, X-ray structure and binding properties of molecular clips based on dimethylpropanediurea
Jansen R.J., Rowan A.E., Scheeren H.W., Nolte R.J., Jansen R.J., de Gelder R.
Chemical Communications, 1998
21.
Polycatenated Two-Dimensional Polyrotaxane Net
Whang D., Kim K.
Journal of the American Chemical Society, 1997