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

被引：59
|
作者：
Kravchenko, AN
Sigachev, AS
Maksareva, EY
Gazieva, GA
Trunova, NS
Lozhkin, BV
Pivina, TS
Il'in, MM
Lyssenko, KA
Nelyubina, YV
Davankov, VA
Lebedev, OV
Makhova, NN
Tartakovsky, VA
机构：
[1] Russian Acad Sci, ND Zelinskii Organ Chem Inst, Moscow 119991, Russia
[2] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia
来源：
RUSSIAN CHEMICAL BULLETIN | 2005年 / 54卷 / 03期
基金：
俄罗斯基础研究基金会;
关键词：
glycolurils; chirality; 4,5-dihydroxyimidazolidin-2-ones; mono- and dialkyl-ureas; quantum-chemical calculations; enantionteric analysis and separation; regioselectivity;
D O I：
10.1007/s11172-005-0307-3
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
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-dihydroxyimidazolidin-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.
引用
收藏
页码：691 / 704
页数：14
相关论文
共 50 条
  • [1] Synthesis of new chiral mono-, di-, tri-, and tetraalkylglycolurils
    A. N. Kravchenko
    A. S. Sigachev
    E. Yu. Maksareva
    G. A. Gazieva
    N. S. Trunova
    B. V. Lozhkin
    T. S. Pivina
    M. M. Il’in
    K. A. Lyssenko
    Yu. V. Nelyubina
    V. A. Davankov
    O. V. Lebedev
    N. N. Makhova
    V. A. Tartakovsky
    Russian Chemical Bulletin, 2005, 54 : 691 - 704
  • [2] Tensammetry of homogeneous mono-, di- and tri- ethoxydodecylethers
    Borkowska, Magdalena
    Szymanski, Andrzej
    Lukaszewski, Zenon
    CHEMIA ANALITYCZNA, 2007, 52 (06): : 1059 - 1069
  • [3] Synthesis of mono-, di-, tri- and tetracarboxy azaphthalocyanines as potential dark quenchers
    Department of Pharmaceutical Chemistry and Drug Control, Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, Heyrovskeho 1203, Hradec Kralove 50005, Czech Republic
    不详
    不详
    Dyes Pigm., 2 (112-119):
  • [4] Synthesis of mono-, di-, tri- and tetracarboxy azaphthalocyanines as potential dark quenchers
    Kopecky, Kamil
    Satinsky, Dalibor
    Novakova, Veronika
    Miletin, Miroslav
    Svoboda, Antonin
    Zimcik, Petr
    DYES AND PIGMENTS, 2011, 91 (02) : 112 - 119
  • [5] Mono-, di-, tri- and tetraphosphatriafulvenes:: Electronic structure and aromaticity
    Holtzl, Tibor
    Nguyen, Minh Tho
    Veszpremi, Tamas
    JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 2007, 811 (1-3): : 27 - 35
  • [6] Mono-, di-, tri- ... polynucleosome, oligonucleosome, nucleofilament, nucleoplasmin: a terminological comment
    Battaglia, E
    CARYOLOGIA, 2000, 53 (3-4) : 169 - 173
  • [7] PREPARATION OF MONO-, DI-, TRI-, TETRA-, AND PENTA-ETHYLENEGLYCOLCHLOROHYDRIN
    ABE, Y
    WATANABE, S
    KOGYO KAGAKU ZASSHI, 1961, 64 (07): : 1192 - &
  • [8] The synthesis of diisobutyl mono-, di- and tri-hydroxyphenols
    Niederl, JB
    Natelson, S
    Beekman, EM
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1933, 55 : 2571 - 2575
  • [9] SYNTHESIS OF SOME MACROCYCLIC DIIMINES FROM MONO-, DI-, TRI-, AND TETRA-INDOLYL DIALDEHYDES
    Somphol, Kittya
    Kumar, Naresh
    Black, David StC
    HETEROCYCLES, 2021, 102 (04) : 686 - 704
  • [10] Solid-phase synthesis of symmetrical 5′,5′-dinucleoside mono-, di-, tri-, and tetraphosphodiesters
    Ahmadibeni, Yousef
    Parang, Keykavous
    ORGANIC LETTERS, 2007, 9 (22) : 4483 - 4486
12345