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Synthesis of trialkyl semithioglycolurils from alkylthiourea-glyoxal cyclic adducts and dialkylureas

Anton Andreevich Galochkin 1
Anton Andreevich Galochkin
, 
Vladimir Vladimirovich Baranov 1
Vladimir Vladimirovich Baranov
, 
Natal'ya Georgievna Kolotyrkina 1
Natal'ya Georgievna Kolotyrkina
, 
Angelina Nikolaevna Kravchenko 1
Angelina Nikolaevna Kravchenko
10.1016/j.mencom.2022.11.021
Published 2022-10-21
Communication , Volume 32, Issue 6, 771-773
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Galochkin A. A. et al. Synthesis of trialkyl semithioglycolurils from alkylthiourea-glyoxal cyclic adducts and dialkylureas // Mendeleev Communications. 2022. Vol. 32. No. 6. pp. 771-773.
GOST all authors (up to 50) Copy
Galochkin A. A., Baranov V. V., Kolotyrkina N. G., Kravchenko A. N. Synthesis of trialkyl semithioglycolurils from alkylthiourea-glyoxal cyclic adducts and dialkylureas // Mendeleev Communications. 2022. Vol. 32. No. 6. pp. 771-773.
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TY - JOUR
DO - 10.1016/j.mencom.2022.11.021
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.11.021
TI - Synthesis of trialkyl semithioglycolurils from alkylthiourea-glyoxal cyclic adducts and dialkylureas
T2 - Mendeleev Communications
AU - Galochkin, Anton Andreevich
AU - Baranov, Vladimir Vladimirovich
AU - Kolotyrkina, Natal'ya Georgievna
AU - Kravchenko, Angelina Nikolaevna
PY - 2022
DA - 2022/10/21
PB - Mendeleev Communications
SP - 771-773
IS - 6
VL - 32
ER -
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@article{2022_Galochkin,
author = {Anton Andreevich Galochkin and Vladimir Vladimirovich Baranov and Natal'ya Georgievna Kolotyrkina and Angelina Nikolaevna Kravchenko},
title = {Synthesis of trialkyl semithioglycolurils from alkylthiourea-glyoxal cyclic adducts and dialkylureas},
journal = {Mendeleev Communications},
year = {2022},
volume = {32},
publisher = {Mendeleev Communications},
month = {Oct},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.11.021},
number = {6},
pages = {771--773},
doi = {10.1016/j.mencom.2022.11.021}
}
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Galochkin, Anton Andreevich, et al. “Synthesis of trialkyl semithioglycolurils from alkylthiourea-glyoxal cyclic adducts and dialkylureas.” Mendeleev Communications, vol. 32, no. 6, Oct. 2022, pp. 771-773. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.11.021.

Keywords

1,4,6-trialkylsemithioglycolurils
4,5-dihydroxyimidazolidin-2-ones
4,5-dihydroxyimidazolidine-2- thiones
alkylthioureas
dialkylureas
one-pot synthesis

Abstract

Condensation of 1-alkyl-4,5-dihydroxyimidazolidine-2-thiones (monoalkylthiourea-glyoxal cyclic adducts) with 1,3-dialkylureas affords novel 1,4,6-trialkylsemithio- glycolurils having non-substituted NH group linked to C=S function. Such compounds can be accessed in two-stage one-pot reaction sequence from alkylthioureas and glyoxal followed by treatment of the resulting adduct with 1,3-dialkylureas

References

1.
Synthesis of glycolurils and their analogues
Kravchenko A.N., Baranov V.V., Gazieva G.A.
Russian Chemical Reviews, 2018
2.
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
3.
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
4.
Baranov V.V., Vol'khina T.N., Kolotyrkina N.G., Kravchenko A.N.
Mendeleev Communications, 2022
5.
Hierarchical structure of a self-assembled xerogel
Kölbel M., Menger F.M.
Chemical Communications, 2001
6.
A New Anion Receptor with a Glycoluril Molecular Scaffold
Kang J., Ju H., Jo J.
Supramolecular Chemistry, 2004
10.
Experimental Pharmacokinetics of Bicaret
Prokopov A.A., Berlyand A.S., Kazantseva O.N.
Pharmaceutical Chemistry Journal, 2003
11.
Multicomponent, hydrogen-bonded cylindrical capsules.
Ajami D., Rebek J.
Journal of Organic Chemistry, 2009
12.
Expanding capsules
Ajami D., Rebek J.
Supramolecular Chemistry, 2009
13.
Soft templates in encapsulation complexes
Ajami D., Liu L., Rebek Jr. J.
Chemical Society Reviews, 2015
14.
Bambusuril Anion Receptors
Lizal T., Sindelar V.
Israel Journal of Chemistry, 2017
15.
Molecular clips and cages derived from glycoluril
Sijbesma R.P., Nolte R.J.
Topics in Current Chemistry, 1995
16.
Glycoluril–tetrathiafulvalene molecular clips: on the influence of electronic and spatial properties for binding neutral accepting guests
Cotelle Y., Hardouin-Lerouge M., Legoupy S., Alévêque O., Levillain E., Hudhomme P.
Beilstein Journal of Organic Chemistry, 2015
17.
Molecular clips and tweezers hosting neutral guests
Hardouin–Lerouge M., Hudhomme P., Sallé M.
Chemical Society Reviews, 2011
18.
Cucurbiturils: from synthesis to high-affinity binding and catalysis
Assaf K.I., Nau W.M.
Chemical Society Reviews, 2015
19.
Investigation on strength properties of polymer modified concrete using glycoluril
Pothinathan S., Muthukannan M., Selvapalam N., Gnanaraj S.C.
International Review of Applied Sciences and Engineering, 2021
21.
(c) M. Shin, M. H. Kim, T. H. Ha, J. Jeon, K.-H. Chung, J. S. Kim and Y. G. Kim, Tetrahedron, 2014, 70, 1617
22.
(d) B. Lee, M. Shin, Y. Seo, M. H. Kim, H. R. Lee, J. S. Kim, K. Chung, D. Yoo and Y. G. Kim, Tetrahedron, 2018, 74, 130
23.
(e) B. Lee, N. Kim, S. Jang, J. H. Park, M. Song, K. Kwon, S. Kim and Y. G. Kim, J. Ind. Eng. Chem., 2022, 113, 360
24.
Glycoluril as a Slow Release Nitrogen Fertilizer
Shimizu T.
Soil Science and Plant Nutrition, 1987
25.
(a) E. Berdimurodov, A. Kholikov, K. Akbarov, L. Guo, S. Kaya, D. K. Verma, M. Rbaa and O. Dagdag, J. Electroanal. Chem., 2022, 907, 116055; (b) P. Patel, S. Nandi, T. Menapara, A. V. Biradar, R. K. Nagarale, N. H. Khan and R. I. Kureshy, Appl. Catal., A, 2018, 565, 127; (c) V. S. Mane, A. S. Kumbhar and R. P. Thummel, Dalton Trans., 2017, 46, 12901; (d) M. Zarei, H. Sepehrmansourie, M. A. Zolfigol, R. Karamian and S. H. M. Farida, New J. Chem., 2018, 42, 14308; (e) J. P. Bruekers, J. A. A. W. Elemans and R. J. M. Nolte, in Supramolecular Catalysis: New Directions and Developments, eds. P. W. N. M. van Leeuwen and M. Raynal, Wiley-VCH, 2022, ch. 21, pp. 303–320; (f) L. Isaacs and D. Witt, Angew. Chem., Int. Ed., 2002, 41, 1905; (g) W. Sliwa, G. Matusiak and J. Peszke, Heterocycles, 2004, 63, 419; (h) Ya. A. Barsegyan, V. V. Baranov and A. N. Kravchenko, Chem.
26.
Methods for substitution of the thioxo group with the oxo group in imidazolidine-2-thione derivatives
Kuptsova A.O., Vinogradova E.E., Kravchenko A.N., Gazieva G.A.
Russian Chemical Bulletin, 2022
27.
Baranov V.V., Barsegyan Y.A., Strelenko Y.A., Karnoukhova V.A., Kravchenko A.N.
Mendeleev Communications, 2020
28.
Baranov V.V., Barsegyan Y.A., Kolotyrkina N.G., Kravchenko A.N.
Mendeleev Communications, 2019
29.
Dual-Functional Semithiobambusurils
Singh M., Solel E., Keinan E., Reany O.
Chemistry - A European Journal, 2014
30.
Semithiobambus[6]uril is a transmembrane anion transporter.
Lang C., Mohite A., Deng X., Yang F., Dong Z., Xu J., Liu J., Keinan E., Reany O.
Chemical Communications, 2017
31.
Hetero-Bambusurils
Reany O., Mohite A., Keinan E.
Israel Journal of Chemistry, 2018
32.
Equatorial Sulfur Atoms in Bambusurils Spawn Cavity Collapse
Mondal P., Solel E., Mitra S., Keinan E., Reany O.
Organic Letters, 2019
36.
New access to thioglycolurils by condensation of 4,5-dihydroxyimidazolidin-2-ones(thiones) with HSCN
Baranov V.V., Nelyubina Y.V., Kravchenko A.N., Kolotyrkina N.G., Biriukova K.A.
Tetrahedron Letters, 2015
37.
Synthesis and Structure of 1-Substituted Semithioglycolurils
Baranov V.V., Galochkin A.A., Nelyubina Y.V., Kravchenko A.N., Makhova N.N.
Synthesis, 2020
38.
Dimroth-type N/S-interchange ofN-aminothioglycolurils in the synthesis of 2-hydrazonoimidazo[4,5-d]thiazolones
Vinogradova E.E., Gazieva G.A., Izmest'ev A.N., Karnoukhova V.A., Kravchenko A.N.
RSC Advances, 2021
39.
Efficient method for the synthesis of 1,3-unsubstituted 2-imino-5-oxooctahydroimidazo[4,5-d]imidazolium iodides based on thioglycolurils
Baranov V.V., Yatsenko E.L., Melnikova E.K., Nelyubina Y.V., Kravchenko A.N.
Chemistry of Heterocyclic Compounds, 2019
40.
Diastereoselective synthesis of 4,5-dihydroxyimidazolidin-2-ones (-thiones) and their structure
Kravchenko A.N., Baranov V.V., Nelyubina Y.V., Gazieva G.A., Svitan’ko I.V.
Russian Chemical Bulletin, 2012
41.
Reactions of sulfonamides with 4,5-dihydroxyimidazolidin-2-ones
Gazieva G.A., Kravchenko A.N., Lebedev O.V., Strelenko Y.A., Chegaev K.Y.
Russian Chemical Bulletin, 1998
42.
Chelate effects in sulfate binding by amide/urea-based ligands
Jia C., Wang Q., Begum R.A., Day V.W., Bowman-James K.
Organic and Biomolecular Chemistry, 2015
43.
Design, synthesis and in vitro evaluation of the hybrids of oxindolylidene and imidazothiazolotriazine as efficient antiproliferative agents
Izmest’ev A.N., Anikina L.V., Zanin I.E., Kolotyrkina N.G., Izmalkova E.S., Kravchenko A.N., Gazieva G.A.
New Journal of Chemistry, 2022
44.
Convenient one-pot formation of highly functionalized 5-bromo-2-aminothiazoles, potential endocannabinoid hydrolase MAGL inhibitors
Prevost J.R., Kozlova A., Es Saadi B., Yildiz E., Modaffari S., Lambert D.M., Pochet L., Wouters J., Dolušić E., Frédérick R.
Tetrahedron Letters, 2018
45.
Baranov V.V., Vol'khina T.N., Nelyubina Y.V., Kravchenko A.N.
Mendeleev Communications, 2021
46.
An efficient approach to dispacamide A and its derivatives
Guihéneuf S., Paquin L., Carreaux F., Durieu E., Meijer L., Bazureau J.P.
Organic and Biomolecular Chemistry, 2012