Synthesis of new chiral mono-, di-, tri-, and tetraalkylglycolurils

Synthesis of new chiral mono-, di-, tri-, and tetraalkylglycolurils Full article

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2005, Volume: 54, Number: 3, Pages: 691-704 Pages count : 14 DOI: 10.1007/s11172-005-0307-3

Authors

Kravchenko A.N. ¹ , Sigachev A.S. ¹ , Maksareva E.Yu. ¹ , Gazieva G.A. ¹ , Trunova N.S. ¹ , Lozhkin B.V. ¹ , Pivina T.S. ¹ , Il’in M.M. ² , Lyssenko K.A. ² , Nelyubina Yu.V. ² , Davankov V.A. ² , Lebedev O.V. ¹ , Makhova N.N. ¹ , Tartakovsky V.A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
2	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, Russian Federation

Two general procedures were developed for the synthesis of chiral N-mono-, N, N′-di-, N, N′ N″-tri-, and N, N′, N″, N′″-tetraalkylglycolurils based on the reactions of 4,5-dihydroxy-imidazolidin-2-ones or glyoxal with one or two moles of alkylureas, respectively, by acid catalysis. The reactions of N-monoalkyl- and N, N′-dialkylureas with glyoxal proceed regioselectively. The mechanism of these reactions was suggested and partly confirmed by quantum-chemical calculations and experimental data. The enantiomeric separation of some chiral glycolurils by chiral-phase HPLC was carried out for the first time.

Kravchenko A.N. , Sigachev A.S. , Maksareva E.Y. , Gazieva G.A. , Trunova N.S. , Lozhkin B.V. , Pivina T.S. , Il’in M.M. , Lyssenko K.A. , Nelyubina Y.V. , Davankov V.A. , Lebedev O.V. , Makhova N.N. , Tartakovsky V.A.
Synthesis of new chiral mono-, di-, tri-, and tetraalkylglycolurils
Russian Chemical Bulletin. 2005. V.54. N3. P.691-704. DOI: 10.1007/s11172-005-0307-3 WOS Scopus OpenAlex

Web of science:	WOS:000232042300024
Scopus:	2-s2.0-25144482929
OpenAlex:	W2143071656

DB	Citing
OpenAlex	40
Scopus	40
Web of science	60