New access to thioglycolurils by condensation of 4,5-dihydroxyimidazolidin-2-ones(thiones) with HSCN

被引：26
作者：
Baranov, Vladimir V. [1 ]
Nelyubina, Yulia V. [2 ]
Kravchenko, Angelina N. [1 ]
Kolotyrkina, Natalya G. [1 ]
Biriukova, Ksenia A. [1 ]
机构：
[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Moscow 119991, Russia
[2] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia
来源：
TETRAHEDRON LETTERS | 2015年 / 56卷 / 44期
基金：
俄罗斯基础研究基金会;
关键词：
Thioglycolurils; Imidazolidin-2-one(thione); HSCN; Condensation; ALPHA-THIOUREIDOALKYLATION; CRYSTAL-STRUCTURE; ORGANOCATALYST; INHIBITORS; CHEMISTRY; EFFICIENT; THIOUREA; UREAS;
D O I：
10.1016/j.tetlet.2015.09.071
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A general and highly effective protocol for the direct synthesis of mono- and dithioglycolurils containing various substituents at the 1,3-nitrogen atoms has been developed based on the condensation of easily accessible dihydroxyimidazolidin-2-ones with HSCN under mild reactions conditions. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6085 / 6088
页数：4
相关论文
共 41 条
  • [1] α-Thioureidoalkylation of functionally substituted ureas: I. Tandem cyclization and esterification in reactions of N-(carboxyalkyl)ureas with 1,3-dialkyl-4,5-dihydroxy-4,5-diphenylimidazolidine-2-thiones in alcohols
    Baranov, V. V.
    Gazieva, G. A.
    Nelyubina, Yu. V.
    Kravchenko, A. N.
    Makhova, N. N.
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 47 (10) : 1564 - 1571
  • [2] Synthesis of new ring-fused thiocarbamates by condensation of 2-thioxo- and 2-oxo-1,3-dialkyl-4,5-dihydroxy-4,5-diphenylimidazolidines with KSCN
    Baranov, Vladimir V.
    Kravehenko, Angelina N.
    Nelyubina, Yulia V.
    [J]. MENDELEEV COMMUNICATIONS, 2014, 24 (02) : 105 - 107
  • [3] Sustainable Synthesis of Thioimidazoles via Carbohydrate-Based Multicomponent Reactions
    Baumann, Marcus
    Baxendale, Ian R.
    [J]. ORGANIC LETTERS, 2014, 16 (23) : 6076 - 6079
  • [4] Studies of the Hydrolytic Stability of the Biologically Active Substance Bicaret
    Berlyand, A. S.
    Prokopov, A. A.
    [J]. PHARMACEUTICAL CHEMISTRY JOURNAL, 2014, 48 (05) : 347 - 349
  • [5] Chemico-Pharmaceutical Analysis of the Biologically Active Substances Albicar
    Berlyand, A. S.
    Lebedev, O. V.
    Prokopov, A. A.
    [J]. PHARMACEUTICAL CHEMISTRY JOURNAL, 2013, 47 (03) : 176 - 178
  • [6] MECHANISTIC STUDIES IN THE CHEMISTRY OF THIOUREA .2. REACTION WITH BENZIL IN ACID-SOLUTION
    BROAN, CJ
    BUTLER, AR
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1991, (10): : 1501 - 1504
  • [7] Thioglycoluril as a Novel Organocatalyst: Rapid and Efficient α-Monobromination of 1,3-Dicarbonyl Compounds
    Cao, Liping
    Ding, Jiaoyang
    Yin, Guodong
    Gao, Meng
    Li, Yitao
    Wu, Anxin
    [J]. SYNLETT, 2009, (09) : 1445 - 1448
  • [8] A facile preparation of thioglycolurils from glycolurils, and regioselectivity in thioglycoluril template-directed crossed-Claisen condensations
    Cow, CN
    Harrison, PHM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (25) : 8834 - 8840
  • [9] Biotin Analogues with Antibacterial Activity Are Potent Inhibitors of Biotin Protein Ligase
    da Costa, Tatiana P. Soares
    Tieu, William
    Yap, Min Y.
    Zvarec, Ondrej
    Bell, Jan M.
    Turnidge, John D.
    Wallace, John C.
    Booker, Grant W.
    Wilce, Matthew C. J.
    Abell, Andrew D.
    Polyak, Steven W.
    [J]. ACS MEDICINAL CHEMISTRY LETTERS, 2012, 3 (06): : 509 - 514
  • [10] BASE-CATALYSED REACTION OF SUBSTITUTED BENZILES WITH UREA AND THIOUREA TO GLYCOLURILES HYDANTOINS AND IMIDAZOLIDONES OR DITHIOGLYCOLURILES AND THIOHYDANTOINS
    DIETZ, W
    MAYER, R
    [J]. JOURNAL FUR PRAKTISCHE CHEMIE, 1968, 37 (1-2): : 78 - &
12345