Abstract:
A new synthetic approach to 2,8-disubstituted 1,5-diphenylglycolurils is based on condensation of 1-(hydroxyalkyl)ureas (ureido alcohols) with tetrahydroimidazooxazolone and tetrahydroimidazooxazinone derivatives which were unexpectedly obtained by acid-catalyzed reaction of ureido alcohols with benzil. An X-ray diffraction study of the supramolecular organization of the obtained compounds revealed the chirality of the crystals of achiral glycoluril molecules.
Citation:
V. V. Baranov, M. M. Antonova, Yu. V. Nelyubina, N. G. Kolotyrkina, I. E. Zanin, A. N. Kravchenko, N. N. Makhova, “Regioselective synthesis of 2,8-disubstituted 1,5-diphenylglycolurils”, Mendeleev Commun., 24:3 (2014), 173–175
Linking options:
https://www.mathnet.ru/eng/mendc2514
https://www.mathnet.ru/eng/mendc/v24/i3/p173
This publication is cited in the following 13 articles:
V. V. Baranov, M. M. Antonova, S. A. Aksenova, N. G. Kolotyrkina, A. N. Kravchenko, Mendeleev Commun., 35:1 (2025), 27–30
V. V. Baranov, M. M. Antonova, S. A. Aksenova, N. G. Kolotyrkina, A. N. Kravchenko, “Novel synthesis of 1,6- and 1,4-dialkyl glycolurils and their supramolecular organization”, Mendeleev Commun., 34:6 (2024), 871–874
V. V. Baranov, V. V. Rusak, A. N. Kravchenko, “Synthesis of 1-aryl-4,5-diphenyl-1H-imidazol-2(3H)-ones”, Russ Chem Bull, 71:9 (2022), 2016
V. V. Baranov, T. N. Vol'khina, N. G. Kolotyrkina, A. N. Kravchenko, “Synthesis and crystal structures of novel glycoluril carboxylic acids conglomerates”, Mendeleev Commun., 32:4 (2022), 537–539
A. V. Smolobochkin, A. S. Gazizov, A. R. Burilov, M. A. Pudovik, O. G. Sinyashin, “Advances in the synthesis of heterocycles bearing an endocyclic urea moiety”, Russian Chem. Reviews, 90:3 (2021), 395–417
S. Yu. Panshina, O. V. Ponomarenko, A. A. Bakibaev, V. S. Malkov, “ANALYSIS OF XRD STRUCTURAL PARAMETERS OF GLYCOLURIL AND ITS DERIVATIVES”, J Struct Chem, 61:9 (2020), 1315
Vitalii A. Palchykov, Alexandr A. Gaponov, Advances in Heterocyclic Chemistry, 131, 2020, 285
N. N. Makhova, L. I. Belen'kii, G. A. Gazieva, I. L. Dalinger, L. S. Konstantinova, V. V. Kuznetsov, A. N. Kravchenko, M. M. Krayushkin, O. A. Rakitin, A. M. Starosotnikov, L. L. Fershtat, S. A. Shevelev, V. Z. Shirinian, V. N. Yarovenko, “Progress in the chemistry of nitrogen-, oxygen- and sulfur-containing heterocyclic systems”, Russian Chem. Reviews, 89:1 (2020), 55–124
L. Spiteri, U. Baisch, L. Vella-Zarb, “Correlations and statistical analysis of solvent molecule hydrogen bonding – a case study of dimethyl sulfoxide (DMSO)”, CrystEngComm, 20:9 (2018), 1291
A. N. Kravchenko, V. V. Baranov, G. A. Gazieva, “Synthesis of glycolurils and their analogues”, Russian Chem. Reviews, 87:1 (2018), 89–108
Vladimir V. Baranov, Maria M. Antonova, Valentina A. Karnoukhova, Angelina N. Kravchenko, “Unexpected reductive transformation of 1-substituted 5-hydroxy-4,5-diphenyl-1 H -imidazol-2(5 H )-ones and their cyclic analogs by the reaction with thiourea and hydrochloric acid”, Tetrahedron Letters, 58:23 (2017), 2203
Maria M. Antonova, Vladimir V. Baranov, Angelina N. Kravchenko, “Methods for the synthesis of 1-substituted 1H-imidazol-2(3H)-ones”, Chem Heterocycl Comp, 51:5 (2015), 395
Vladimir V. Baranov, Maria M. Antonova, Yulia V. Nelyubina, Natal'ya G. Kolotyrkina, Igor E. Zanin, Angelina N. Kravchenko, Nina N. Makhova, “ChemInform Abstract: Regioselective Synthesis of 2,8‐Disubstituted 1,5‐Diphenylglycolurils.”, ChemInform, 45:40 (2014)
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