Abstract:
The reactions of 4,5-dihydroxyimidazolidin-2-one with chiral S- and R-N-carbamoyl-α-amino acids occur diastereoselectively with the formation of corresponding 1R,5S(1S,5R)-glycoluriles as predominant diastereomers; the absolute configuration is determined for three stereoisomers by X-ray diffraction analysis.
Document Type:
Article
Language: English
Citation:
A. N. Kravchenko, K. Yu. Chegaev, I. E. Chikunov, P. A. Belyakov, E. Yu. Maksareva, K. A. Lyssenko, O. V. Lebedev, N. N. Makhova, “Highly diastereoselective synthesis of 2-monosubstituted 1R,5S(1S,5R)-glycoluriles on the basis of S- and R-N-carbamoyl-α-amino acids”, Mendeleev Commun., 13:6 (2003), 269–271
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https://www.mathnet.ru/eng/mendc4058
https://www.mathnet.ru/eng/mendc/v13/i6/p269
This publication is cited in the following 15 articles:
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
I. S. Ryzhkina, Yu. V. Kiseleva, L. I. Murtazina, O. A. Mishina, A. P. Timosheva, S. Yu. Sergeeva, V. V. Baranov, A. N. Kravchenko, A. I. Konovalov, “Self-organization and chirality in the high dilution solutions of glycoluril enantiomers with (R)- and (S)-methionine moieties”, Mendeleev Commun., 25:1 (2015), 72–74
A. N. Kravchenko, V. V. Baranov, L. V. Anikina, Yu. B. Vikharev, I. S. Bushmarinov, Yu. V. Nelyubina, “Neuroprotective Activity of (+)-(S)-2-[(1S,5R)-(3,7-Dioxo-2,4,6,8-Tetraazabicyclo[3.3.0]oct-2-yl)]-4-methylthiobutanoic acid”, Russ J Bioorg Chem, 38:5 (2012), 550
A. N. Kravchenko, K. A. Lyssenko, I. E. Chikunov, P. A. Belyakov, M. M. Il'in, V. V. Baranov, Yu. V. Nelyubina, V. A. Davankov, T. S. Pivina, N. N. Makhova, M. Yu. Antipin, “4,5-Dihydroxyimidazolidin-2-ones in the α-ureidoalkylation reaction of N-(carboxyalkyl)-, N-(hydroxyalkyl)-, and N-(aminoalkyl)ureas 1. α-Ureidoalkylation of N-(carboxyalkyl)ureas”, Russ Chem Bull, 58:2 (2009), 395
A. N. Kravchenko, E. Yu. Maksareva, S. V. Vasilevskii, O. V. Lebedev, K. A. Lyssenko, “A new approach to the synthesis of 1,3-dimethyl-4,5-disubstituted imidazolidin-2-ones”, Mendeleev Commun., 18:1 (2008), 45–47
V. V. Baranov, A. N. Kravchenko, P. A. Belyakov, N. N. Makhova, “New generation of enantiomerically pure N-α-carboxyalkylglycolurils”, Mendeleev Commun., 18:2 (2008), 96–98
A. N. Kravchenko, G. A. Gazieva, A. S. Sigachev, E. Yu. Maksareva, K. A. Lyssenko, N. N. Makhova, “Two-step α-ureidoalkylation of ureas with 4,5-dihydroxyimidazolidin-2-ones”, Russ Chem Bull, 56:1 (2007), 148
I. E. Chikunov, A. N. Kravchenko, N. N. Makhova, “Synthesis of enantiomerically pure fused polyheterocyclic glycolurils based on (S)- α-amino acids”, Mendeleev Commun., 17:6 (2007), 321–322
A. N. Kravchenko, A. S. Sigachev, G. A. Gazieva, E. Yu. Maksareva, N. S. Trunova, K. A. Chegaev, K. A. Lyssenko, D. V. Lyubetsky, M. I. Struchkova, M. M. Il'in, V. A. Davankov, O. V. Lebedev, N. N. Makhova, V. A. Tartakovsky, “Reaction of N-alkylglycolurils with electrophilic reagents”, Chem Heterocycl Compd, 42:3 (2006), 365
A. S. Sigachev, A. N. Kravchenko, P. A. Belyakov, O. V. Lebedev, N. N. Makhova, “α-Ureidoalkylation of thiosemicarbazide and aminoguanidine”, Russ Chem Bull, 55:5 (2006), 865
Andrey S. Sigachev, Angelina N. Kravchenko, Galina A. Gazieva, Pavel A. Belyakov, Natal'Ya G. Kolotyrkina, Oleg V. Lebedev, Nina N. Makhova, Konstantin A. Lyssenko, “Synthesis of first representatives of 3,3′-bi(6,8-dialkyl-2,4-dioxa-6,8-diazabicyclo[3.3.0]octan-7-ones)”, Journal of Heterocyclic Chemistry, 43:5 (2006), 1295
A. S. Sigachev, A. N. Kravchenko, E. Yu. Maksareva, B. V. Lozhkin, K. A. Lyssenko, N. N. Makhova, “The first synthesis of assemblies of imidazolidine rings by α-ureidoalkylation of imidazolidin-2-one with 4,5-dihydroxyimidazolidin-2-ones”, Mendeleev Commun., 16:2 (2006), 80–82
I. E. Chikunov, A. N. Kravchenko, P. A. Belyakov, O. V. Lebedev, N. N. Makhova, “Synthesis of (S)-N-hydantoinoalkylglycoluriles by one-pot double cyclisation of chiral α,ω-diureido acids under the action of 4,5-dihydroxyimidazolidin-2-ones”, Mendeleev Commun., 15:2 (2005), 67–69
Angelina N. Kravchenko, Konstantin Yu. Chegaev, Il'ya E. Chikunov, Pavel A. Belyakov, Elena Yu. Maksareva, Konstantin A. Lyssenko, Oleg V. Lebedev, Nina N. Makhova, “Highly Diastereoselective Synthesis of 2‐Monosubstituted 1R,5S(1S,5R)‐Glycoluriles on the Basis of S‐ and R‐N‐Carbamoyl‐α‐amino Acids.”, ChemInform, 35:20 (2004)
I. E. Chikunov, A. N. Kravchenko, P. A. Belyakov, K. A. Lyssenko, V. V. Baranov, O. V. Lebedev, N. N. Makhova, “Synthesis of 1S,5R- and 1R,5S-glycoluriles by diastereospecific α-ureidoalkylation of (S)/(R)-N-carbamoyl-α-amino acids with 4,5-dihydroxyimidazolidin-2-one”, Mendeleev Commun., 14:6 (2004), 253–255
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