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Highly regioselective synthesis and structure of 1-substituted 3a,6,6a-triphenylglycolurils

Vladimir Vladimirovich Baranov 1
Vladimir Vladimirovich Baranov
Maria Mikhailovna Antonova 2
Maria Mikhailovna Antonova
Svetlana Aleksandrovna Aksenova
Natalya Georgievna Kolotyrkina 1
Natalya Georgievna Kolotyrkina
Angelina Nikolaevna Kravchenko 1
Angelina Nikolaevna Kravchenko
2 State Research Institute of Organic Chemistry and Technology, 111024 Moscow, Russian Federation
4 Moscow Center for Advanced Studies, 123592 Moscow, Russian Federation
Published 2025-01-24
CommunicationVolume 35, Issue 1, 27-30
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Baranov V. V. et al. Highly regioselective synthesis and structure of 1-substituted 3a,6,6a-triphenylglycolurils // Mendeleev Communications. 2025. Vol. 35. No. 1. pp. 27-30.
GOST all authors (up to 50) Copy
Baranov V. V., Antonova M. M., Aksenova S. A., Kolotyrkina N. G., Kravchenko A. N. Highly regioselective synthesis and structure of 1-substituted 3a,6,6a-triphenylglycolurils // Mendeleev Communications. 2025. Vol. 35. No. 1. pp. 27-30.
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TY - JOUR
DO - 10.71267/mencom.7564
UR - https://mendcomm.colab.ws/publications/10.71267/mencom.7564
TI - Highly regioselective synthesis and structure of 1-substituted 3a,6,6a-triphenylglycolurils
T2 - Mendeleev Communications
AU - Baranov, Vladimir Vladimirovich
AU - Antonova, Maria Mikhailovna
AU - Aksenova, Svetlana Aleksandrovna
AU - Kolotyrkina, Natalya Georgievna
AU - Kravchenko, Angelina Nikolaevna
PY - 2025
DA - 2025/01/24
PB - Mendeleev Communications
SP - 27-30
IS - 1
VL - 35
ER -
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@article{2025_Baranov,
author = {Vladimir Vladimirovich Baranov and Maria Mikhailovna Antonova and Svetlana Aleksandrovna Aksenova and Natalya Georgievna Kolotyrkina and Angelina Nikolaevna Kravchenko},
title = {Highly regioselective synthesis and structure of 1-substituted 3a,6,6a-triphenylglycolurils},
journal = {Mendeleev Communications},
year = {2025},
volume = {35},
publisher = {Mendeleev Communications},
month = {Jan},
url = {https://mendcomm.colab.ws/publications/10.71267/mencom.7564},
number = {1},
pages = {27--30},
doi = {10.71267/mencom.7564}
}
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Baranov, Vladimir Vladimirovich, et al. “Highly regioselective synthesis and structure of 1-substituted 3a,6,6a-triphenylglycolurils.” Mendeleev Communications, vol. 35, no. 1, Jan. 2025, pp. 27-30. https://mendcomm.colab.ws/publications/10.71267/mencom.7564.

Keywords

1-alkylimidazolones
1-phenylurea
glycolurils
regioselective condensation
supramolecular organization
tetrahydroimidazo[5,1-b][1,3]oxazol-5(6H)-one
X-ray

Abstract

The reactions of 1-alkyl-5-hydroxy-4,5-diphenyl-1,5-di-hydro-2H-imidazol-2-ones or 7-hydroxy-7,7a-diphenyltetrahydroimidazo[5,1-b][1,3]oxazol-5(6H)-one with 1-phenylurea selectively afford new 1-substituted 3a,6,6a-triphenylglycolurils. Crystals of four representatives were studied by X-ray diffraction when the formation of two conglomerates was discovered.

Funders

Ministry of Education and Science of the Russian Federation
075-00277-24-00

References

.
OLEX2: a complete structure solution, refinement and analysis program
Dolomanov O.V., Bourhis L.J., Gildea R.J., Howard J.A., Puschmann H.
Journal of Applied Crystallography, 2009
.
Progress in the chemistry of nitrogen-, oxygen- and sulfur-containing heterocyclic systems
Makhova N.N., Belen’kii L.I., Gazieva G.A., Dalinger I.L., Konstantinova L.S., Kuznetsov V.V., Kravchenko A.N., Krayushkin M.M., Rakitin O.A., Starosotnikov A.M., Fershtat L.L., Shevelev S.A., Shirinian V.Z., Yarovenko V.N.
Russian Chemical Reviews, 2020
.
Baranov V.V., Vol'khina T.N., Kolotyrkina N.G., Kravchenko A.N.
Mendeleev Communications, 2022
.
Galochkin A.A., Baranov V.V., Kolotyrkina N.G., Kravchenko A.N.
Mendeleev Communications, 2022
.
Synthesis of glycolurils and their analogues
Kravchenko A.N., Baranov V.V., Gazieva G.A.
Russian Chemical Reviews, 2018
.
Baranov V.V., Antonova M.M., Nelyubina Y.V., Kolotyrkina N.G., Zanin I.E., Kravchenko A.N., Makhova N.N.
Mendeleev Communications, 2014
.
Self-organization of 1,6-dialkyl-3a,6a-diphenylglycolurils in the crystalline state
Karnoukhova V.A., Baranov V.V., Vologzhanina A.V., Kravchenko A.N., Fedyanin I.V.
CrystEngComm, 2021
.
Graph-set analysis of hydrogen-bond patterns in organic crystals
Etter M.C., MacDonald J.C., Bernstein J.
Acta Crystallographica Section B Structural Science, 1990
.
New supramolecular organization for a glycoluril: chiral hydrogen-bonded ribbons
Johnson D.W., Palmer L.C., Hof F., Iovine P.M., Rebek J.
Chemical Communications, 2002
.
Glycoluril ribbons tethered by complementary hydrogen bonds
Johnson D.W., Hof F., Palmer L.C., Martín T., Obst U., Rebek, Jr. J.
Chemical Communications, 2003
.
Anikina L.V., Vikharev Y.B., Baranov V.V., Malyshev O.R., Kravchenko A.N.
Mendeleev Communications, 2018
.
Regioselective synthesis of 1,5-Diaryl-2-(Hydroxyalkyl)-8-Methylglycolurils
Antonova M.M., Baranov V.V., Nelyubina Y.V., Kravchenko A.N.
Chemistry of Heterocyclic Compounds, 2014
.
Chiral Molecular Clips Control Orthogonal Crystalline Organization
Chen Y., She N., Meng X., Yin G., Wu A., Isaacs L.
Organic Letters, 2007
.
Chiral Softballs:  Synthesis and Molecular Recognition Properties
Rivera J.M., Martín T., Rebek J.
Journal of the American Chemical Society, 2001
.
Self-assembled Architectures from Glycoluril
Elemans J.A., Rowan A.E., Nolte R.J.
Industrial & Engineering Chemistry Research, 2000
.
ANALYSIS OF XRD STRUCTURAL PARAMETERS OF GLYCOLURIL AND ITS DERIVATIVES
Panshina S.Y., Ponomarenko O.V., Bakibaev A.A., Malkov V.S.
Journal of Structural Chemistry, 2020
.
Synthesis and separation of cucurbit[n]urils and their derivatives
Cong H., Ni X.L., Xiao X., Huang Y., Zhu Q., Xue S., Tao Z., Lindoy L.F., Wei G.
Organic and Biomolecular Chemistry, 2016
.
Dimeric molecular clips based on glycoluril
Sokolov J., Lizal T., Sindelar V.
New Journal of Chemistry, 2017
.
Recent Advances in the Chemistry of Saturated Annulated Nitrogen-Containing Polycyclic Compounds
Kirsanov V.Y., Rakhimova E.B.
International Journal of Molecular Sciences, 2022
.
Expanding capsules
Ajami D., Rebek J.
Supramolecular Chemistry, 2009
.
Synthesis of Enantiomerically Pure Bambus[6]urils Utilizing Orthogonal Protection of Glycolurils
Slávik P., Torrisi J., Jurček P., Sokolov J., Šindelář V.
Journal of Organic Chemistry, 2023
.
Gorbin S.I., Bakibaev A.A., Kurgachev D.A., Malkov V.S., Novolokov K.Y., Sysoev G.O.
Mendeleev Communications, 2023
.
Methods of synthesizing glycoluril-based macrocyclic compounds as precursors for polymeric compounds
Kabieva S.K., Zhumanazarova G.M., Kanasheva N., Bakibaev A.A., Yu. Panshina S., Malkov V.S., Mamaeva E.A., Knyazev A.S.
Journal of Saudi Chemical Society, 2023
.
The Determination of the Biocompatibility of New Compositional Materials, including Carbamide-Containing Heterocycles of Anti-Adhesion Agents for Abdominal Surgery
Kanasheva N., Fedorishin D.A., Lyapunova M.V., Bukterov M.V., Kaidash O.A., Bakibaev A.A., Yerkassov R., Mashan T., Nesmeyanova R., Ivanov V.V., Udut E.V., Tuguldurova V.P., Salina M.V., Malkov V.S., Knyazev A.S., et. al.
Molecules, 2024
.
Cycloglycolurils: Hybrid Glycoluril–Cyclobenzil Macrocycles
Basavarajappa A., Wang X., Miljanić O.Š.
Organic Letters, 2024
.
Baranov V.V., Antonova M.M., Aksenova S.A., Kolotyrkina N.G., Kravchenko A.N.
Mendeleev Communications, 2024