Efficient method for the synthesis of 1,3-unsubstituted 2-imino-5-oxooctahydroimidazo[4,5-d]imidazolium iodides based on thioglycolurils

被引:5
作者
Baranov, Vladimir V. [1 ]
Yatsenko, Evgeniya L. [1 ,2 ]
Melnikova, Elizaveta K. [3 ,4 ]
Nelyubina, Yulia V. [3 ]
Kravchenko, Angelina N. [1 ]
机构
[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, 47 Leninsky Ave, Moscow 119991, Russia
[2] DI Mendeleev Univ Chem Technol Russia, 9 Miusskaya Sq, Moscow 125047, Russia
[3] Russian Acad Sci, AN Nesmeyanov Inst Organoelement Cpds, 28 Vavilova St, Moscow 119991, Russia
[4] Moscow MV Lomonosov State Univ, 1-3 Leninskie Gory, Moscow 119991, Russia
基金
俄罗斯科学基金会;
关键词
iminoglycolurils; isothiouronium salts; thioglycolurils; condensation; S-methylation;
D O I
10.1007/s10593-019-02433-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile and efficient two-step synthetic route to previously inaccessible 1,3-unsubstituted 2-imino-5-oxooctahydroimidazo[4,5-d]-imidazol-1-ium iodides has been developed using easily accessible thioglycolurils, MeI, and various primary amines, morpholine, or ethylene diamine. The structure of representative products and hydrogen-bonding pattern in their crystals have been investigated by X-ray diffraction.
引用
收藏
页码:160 / 166
页数:7
相关论文
共 17 条
  • [1] Synthesis of five- and six-membered cyclic guanidines by guanylation with isothiouronium iodides and amines under mild conditions
    Aoyagi, Naoto
    Endo, Takeshi
    [J]. SYNTHETIC COMMUNICATIONS, 2017, 47 (05) : 442 - 448
  • [2] A SYNTHESIS OF 2-ALKYLAMINO-4,5-DIHYDROIMIDAZOLES
    ASPINALL, SR
    BIANCO, EJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (02) : 602 - 603
  • [3] New access to thioglycolurils by condensation of 4,5-dihydroxyimidazolidin-2-ones(thiones) with HSCN
    Baranov, Vladimir V.
    Nelyubina, Yulia V.
    Kravchenko, Angelina N.
    Kolotyrkina, Natalya G.
    Biriukova, Ksenia A.
    [J]. TETRAHEDRON LETTERS, 2015, 56 (44) : 6085 - 6088
  • [4] Synthesis, S-alkylation, and fungicidal activity of 4-(benzylideneamino)thioglycolurils
    Gazieva, G. A.
    Nechaeva, T. V.
    Kostikova, N. N.
    Sigay, N. V.
    Serkov, S. A.
    Popkov, S. V.
    [J]. RUSSIAN CHEMICAL BULLETIN, 2018, 67 (06) : 1059 - 1064
  • [5] Synthesis and biological evaluation of new substituted thioglycolurils, their analogues and derivatives
    Gazieva, Galina A.
    Anikina, Lada V.
    Nechaeva, Tatyana V.
    Pukhov, Sergey A.
    Karpova, Tatyana B.
    Popkov, Sergey V.
    Nelyubina, Yulia V.
    Kolotyrkina, Natalya G.
    Kravchenko, Angelina N.
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2017, 140 : 141 - 154
  • [6] Gieling G.T.W., 1996, CHEM COMMUN, P241
  • [7] N-14 NMR-STUDIES ON CYCLIC NITRAMINES - CORRELATIONS OF CHEMICAL-SHIFTS WITH NITROGEN PARTIAL ATOMIC CHARGE AND PI-ORBITAL OVERLAP
    KONY, M
    DAGLEY, IJ
    LESLIE, DR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (19) : 5623 - 5626
  • [8] Synthesis of glycolurils and their analogues
    Kravchenko, Angelina N.
    Baranov, Vladimir V.
    Gazieva, Galina A.
    [J]. RUSSIAN CHEMICAL REVIEWS, 2018, 87 (01) : 89 - 108
  • [9] Luengo J.I., US Patent, Patent No. 6630470
  • [10] Luengo J.I., US Patent, Patent No. 5981551