Home / Publications / Novel synthesis of 1,6- and 1,4-dialkyl glycolurils and their supramolecular organization

Novel synthesis of 1,6- and 1,4-dialkyl glycolurils and their supramolecular organization

Vladimir Vladimirovich Baranov 1
Vladimir Vladimirovich Baranov
, 
Maria Mikhailovna Antonova 2
Maria Mikhailovna Antonova
, 
Svetlana Aleksandrovna Aksenova 3
Svetlana Aleksandrovna Aksenova
, 
Natal'ya Georgievna Kolotyrkina 1
Natal'ya Georgievna Kolotyrkina
, 
Angelina Nikolaevna Kravchenko 1
Angelina Nikolaevna Kravchenko
2 State Research Institute of Organic Chemistry and Technology, Moscow, Russian Federation
3 A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Moscow, Russian Federation
10.1016/j.mencom.2024.10.032
Published 2024-10-22
Communication , Volume 34, Issue 6, 871-874
2
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Baranov V. V. et al. Novel synthesis of 1,6- and 1,4-dialkyl glycolurils and their supramolecular organization // Mendeleev Communications. 2024. Vol. 34. No. 6. pp. 871-874.
GOST all authors (up to 50) Copy
Baranov V. V., Antonova M. M., Aksenova S. A., Kolotyrkina N. G., Kravchenko A. N. Novel synthesis of 1,6- and 1,4-dialkyl glycolurils and their supramolecular organization // Mendeleev Communications. 2024. Vol. 34. No. 6. pp. 871-874.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2024.10.032
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.10.032
TI - Novel synthesis of 1,6- and 1,4-dialkyl glycolurils and their supramolecular organization
T2 - Mendeleev Communications
AU - Baranov, Vladimir Vladimirovich
AU - Antonova, Maria Mikhailovna
AU - Aksenova, Svetlana Aleksandrovna
AU - Kolotyrkina, Natal'ya Georgievna
AU - Kravchenko, Angelina Nikolaevna
PY - 2024
DA - 2024/10/22
PB - Mendeleev Communications
SP - 871-874
IS - 6
VL - 34
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2024_Baranov,
author = {Vladimir Vladimirovich Baranov and Maria Mikhailovna Antonova and Svetlana Aleksandrovna Aksenova and Natal'ya Georgievna Kolotyrkina and Angelina Nikolaevna Kravchenko},
title = {Novel synthesis of 1,6- and 1,4-dialkyl glycolurils and their supramolecular organization},
journal = {Mendeleev Communications},
year = {2024},
volume = {34},
publisher = {Mendeleev Communications},
month = {Oct},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.10.032},
number = {6},
pages = {871--874},
doi = {10.1016/j.mencom.2024.10.032}
}
MLA
Cite this
MLA Copy
Baranov, Vladimir Vladimirovich, et al. “Novel synthesis of 1,6- and 1,4-dialkyl glycolurils and their supramolecular organization.” Mendeleev Communications, vol. 34, no. 6, Oct. 2024, pp. 871-874. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.10.032.

Keywords

1-alkylimidazolones
1-alkylureas
glycolurils
regioselective condensation
supramolecular organization
X-ray

Abstract

New regioselective reaction of 1-alkyl-5-hydroxy-4,5-diphenyl-1H-imidazol-2(5H)-one with alkylureas gives predominantly 1,6-dialkyl-3a,6a-diphenylglycolurils along with minor quantities of the 1,4-isomers. In case of propyl homologues, co-crystal of 1,6/1,4-dipropyl glycolurils would precipitate. Based on the analysis of the crystal packing of the products, new type of supramolecular chains for 1,4-disubstituted glycolurils has been identified.

References

1.
Synthesis of glycolurils and their analogues
Kravchenko A.N., Baranov V.V., Gazieva G.A.
Russian Chemical Reviews, 2018
2.
Regioselective reactions of N-(carboxyalkyl)- and N-(aminoethyl)ureas with glyoxal and 1,2-dioxo-1,2-diphenylethane
Kravchenko A.N., Baranov V.V., Gazieva G.A., Chikunov I.E., Nelyubina Y.V.
Russian Chemical Bulletin, 2014
3.
Novel Method for the Synthesis of Substituted Imidazothiazolones
Nelyubina Y., Baranov V., Kravchenko A., Antonova M.
Synlett, 2015
4.
Baranov V.V., Antonova M.M., Nelyubina Y.V., Kolotyrkina N.G., Zanin I.E., Kravchenko A.N., Makhova N.N.
Mendeleev Communications, 2014
5.
Three-dimensional structures and spectra of 2,6- and 2,8-diethyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-diones
Shamuratov �.B., Batsanov A.S., Struchkov Y.T., Tsivadze A.Y., Tsintsadze M.G., Khmel'nitskii L.I., Simonov Y.A., Dvorkin A.A., Lebedev O.V., Markova T.B.
Chemistry of Heterocyclic Compounds, 1991
6.
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
7.
A short history of SHELX
Sheldrick G.M.
Acta Crystallographica Section A Foundations of Crystallography, 2007
8.
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
9.
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
10.
Multifunctionalized Glycolurils
Pryor K.E., Rebek J.
Organic Letters, 1999
11.
Reasons Why Aldehydes Do Not Generally Participate in Cucurbit[n]uril Forming Reactions
Ma D., Gargulakova Z., Zavalij P.Y., Sindelar V., Isaacs L.
Journal of Organic Chemistry, 2010
12.
Glycoluril Dimer Isomerization under Aqueous Acidic Conditions Related to Cucurbituril Formation
Stancl M., Gargulakova Z., Sindelar V.
Journal of Organic Chemistry, 2012
14.
Glycoluril Dimers Bearing Hydrogen Atoms on Their Convex Face and Their Self-Assembly in the Solid State
Stancl M., Necas M., Taraba J., Sindelar V.
Journal of Organic Chemistry, 2008
15.
“Flexiball” Toolkit:  A Modular Approach to Self-Assembling Capsules
O'Leary B.M., Szabo T., Svenstrup N., Schalley C.A., Lützen A., Schäfer M., Rebek J.
Journal of the American Chemical Society, 2001
16.
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
18.
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
19.
Baranov V.V., Vol'khina T.N., Kolotyrkina N.G., Kravchenko A.N.
Mendeleev Communications, 2022
22.
Galochkin A.A., Baranov V.V., Kolotyrkina N.G., Kravchenko A.N.
Mendeleev Communications, 2022
23.
Anion Receptor with Two Imidazolium Rings on the Glycoluril
Kim H., In S., Kang J.
Supramolecular Chemistry, 2006