Unexpected Formation of Thioglycolurils Precursors

被引:13
作者
Gazieva, Galina A. [1 ]
Kravchenko, Angelina N. [1 ]
机构
[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Moscow 119991, Russia
基金
俄罗斯基础研究基金会;
关键词
ALPHA-THIOUREIDOALKYLATION; MASS-SPECTROMETRY; GLYCOLURIL; CHEMISTRY; TEMPLATE; THIOUREA; UREAS; ACID; UREIDOALKYLATION; CYCLIZATION;
D O I
10.1002/jhet.2305
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Unexpectedly, nitrosation of 5,7-dialkyl-3-thioxoperhydroimidazo[4,5-e]-1,2,4-triazine-6-ones(thiones) with sodium nitrite in glacial AcOH led to 3,3-bis(5,7-dialkyl-1-nitroso-6-oxo(thioxo)-1,4,4a,5,7,7a-hexahydroimidazo[4,5-e]-1,2,4-triazinyl)disulfides that decomposed spontaneously into 1,3-dialkyl-5-thioxohexahydroimidazo[4,5-d]imidazol-2(1H)-ones(thiones) in DMSO-d(6) in the presence of water.
引用
收藏
页码:1858 / 1863
页数:6
相关论文
共 46 条
  • [31] Petersen H., 1973, Synthesis, V1973, P243
  • [32] Multifunctionalized glycolurils
    Pryor, KE
    Rebek, J
    [J]. ORGANIC LETTERS, 1999, 1 (01) : 39 - 42
  • [33] Kinetics of glycoluril template-directed Claisen condensations and mechanistic implications
    Rahimizadeh, M
    Kam, K
    Jenkins, SI
    McDonald, RS
    Harrison, PHM
    [J]. CANADIAN JOURNAL OF CHEMISTRY, 2002, 80 (05) : 517 - 527
  • [34] SDBS, 21641 SDBS NAT I ADV
  • [35] Supramolecular Rhombic Grids Formed from Bimolecular Building Blocks
    She, Neng-Fang
    Gao, Meng
    Meng, Xiang-Gao
    Yang, Guang-Fu
    Elemans, Johannes A. A. W.
    Wu, An-Xin
    Isaacs, Lyle
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (33) : 11695 - +
  • [36] α-ureidoalkylation of thiosemicarbazide and aminoguanidine
    Sigachev, A. S.
    Kravchenko, A. N.
    Belyakov, P. A.
    Lebedev, O. V.
    Makhova, N. N.
    [J]. RUSSIAN CHEMICAL BULLETIN, 2006, 55 (05) : 865 - 872
  • [37] Synthesis of first representatives of 3,3′-bi(6,8-dialkyl-2,4-dioxa-6,8-diazabicyclo[3.3.0]octan-7-ones)
    Sigachev, Andrey S.
    Kravchenko, Angelina N.
    Gazieva, Galina A.
    Belyakov, Pavel A.
    Kolotyrkina, Natal'ya G.
    Lebedev, Oleg V.
    Makhova, Nina N.
    Lyssenko, Konstantin A.
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2006, 43 (05) : 1295 - 1302
  • [38] The Synthetic Challenge of Thioglycolurils
    Singh, Mandeep
    Parvari, Galit
    Botoshansky, Mark
    Keinan, Ehud
    Reany, Ofer
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (05) : 933 - 940
  • [39] Glycoluril Dimer Isomerization under Aqueous Acidic Conditions Related to Cucurbituril Formation
    Stancl, Marek
    Gargulakova, Zuzana
    Sindelar, Vladimir
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (23) : 10945 - 10948
  • [40] Glycoluril Trimers: Selective Synthesis and Supramolecular Properties
    Stancl, Marek
    Hodan, Martin
    Sindelar, Vladimir
    [J]. ORGANIC LETTERS, 2009, 11 (18) : 4184 - 4187