Skeletal rearrangement of arylmethylideneimidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine-2,7-diones in the synthesis of the corresponding imidazo[4,5-e]thiazolo[2,3-c]-1,2,4-triazine-2,8-diones

被引:15
|
作者
Izmest'ev, Alexei N. [1 ]
Vasileva, Darya A. [1 ,2 ]
Melnikova, Elizaveta K. [3 ,4 ]
Kolotyrkina, Natalya G. [1 ]
Borisova, Irina A. [1 ]
Kravchenko, Angelina N. [1 ]
Gazieva, Galina A. [1 ]
机构
[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Moscow 119991, Russia
[2] DI Mendeleev Univ Chem Technol Russia, Moscow 125047, Russia
[3] AN Nesmeyanov Inst Organoelement Cpds, Moscow 119991, Russia
[4] Lomonosov Moscow State Univ, Moscow 119991, Russia
基金
俄罗斯基础研究基金会;
关键词
BIOLOGICAL-ACTIVITY; ANTICANCER ACTIVITY; DERIVATIVES; DESIGN; INHIBITORS; DISCOVERY;
D O I
10.1039/c8nj05058a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Z)-1,3-Dialkyl-7-arylmethylidene-1,3a,4,9a-tetrahydroimidazo[4,5-e]thiazolo[2,3-c]-1,2,4-triazine-2,8(3H,7H)-diones have been prepared via a chemo- and diastereoselective aldol condensation of 1,3-dialkyl-3,3a,9,9a-tetrahydroimidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine-2,7(1H,6H)-diones with aromatic aldehydes followed by the skeletal rearrangement of thiazolotriazine fragments. We succeeded in synthesizing hitherto unknown products of alkali-induced skeletal rearrangement of 3a,9a-diphenyl substituted imidazothiazolotriazines.
引用
收藏
页码:1038 / 1052
页数:15
相关论文
共 50 条
  • [11] New Conversions and Functionalization Possibilities in Pyrimido[4,5-e][1,2,4]triazine-6,8-diones
    Yu. A. Azev
    D. Gabel
    U. Doerfler
    M. E. Él'-Zaria
    K. Bauer
    S. V. Shorshnev
    N. A. Klyuev
    Pharmaceutical Chemistry Journal, 2003, 37 (5) : 238 - 242
  • [12] A 1,3-dipolar cycloaddition of azomethine ylides to imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazine oxindolylidene derivatives in the synthesis of novel spirooxindole derivatives
    Izmest'ev, Alexei N.
    Kravchenko, Angelina N.
    Gazieva, Galina A.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2023, 59 (08) : 594 - 603
  • [13] A 1,3-dipolar cycloaddition of azomethine ylides to imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazine oxindolylidene derivatives in the synthesis of novel spirooxindole derivatives
    Alexei N. Izmest’ev
    Angelina N. Kravchenko
    Galina A. Gazieva
    Chemistry of Heterocyclic Compounds, 2023, 59 : 594 - 603
  • [14] Regioselective synthesis of new imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines via reaction of imidazo[4,5-e][1,2,4]triazinethiones with ethyl phenylpropiolate
    Vinogradov, Dmitry B.
    Izmest'ev, Alexei N.
    Kravchenko, Angelina N.
    Kolotyrkina, Natalya G.
    Gazieva, Galina A.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2024, 61 (01) : 137 - 145
  • [15] Synthesis of thiazolo[4,5-e][1,2,4]triazolo[1,5-c]pyrimidine derivatives
    Lee, Hyuck Joo
    Kim, Sung Min
    Song, Yang-Heon
    HETEROCYCLIC COMMUNICATIONS, 2013, 19 (02) : 101 - 104
  • [16] One-pot regioselective synthesis of new imidazo[4,5-e]thiazolo[3,2-b][1,2,4]triazines by reaction of imidazotriazines with propargyl bromide
    Vinogradova, Ekaterina E. E.
    Kravchenko, Angelina N. N.
    Gazieva, Galina A. A.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2023, 60 (09) : 1609 - 1618
  • [17] A new simple approach to the preparation of imidazo[4,5-e]-1,2,4-triazine derivatives
    Sigachev, AS
    Kravchenko, AN
    Lyssenko, KA
    Belyakov, PA
    Lebedev, OV
    Makhova, NN
    MENDELEEV COMMUNICATIONS, 2003, (04) : 190 - 192
  • [18] Synthesis of new heterylmethylidene derivatives of isomeric imidazo[4,5-e]thiazolo-fused [1,2,4]triazines
    Lugovoi, Maksim E.
    Izmest'ev, Alexei N.
    Kolotyrkina, Natalya G.
    Izmalkova, Ekaterina S.
    Kravchenko, Angelina N.
    Gazieva, Galina A.
    MENDELEEV COMMUNICATIONS, 2024, 34 (04) : 558 - 560
  • [19] Use of tandem AN-AN reactions for the synthesis of thiazolo[4,5-e]-1,2,4-triazines
    Charushin, VN
    Mochulskaya, NN
    Andreiko, AA
    Kodess, MI
    Chupakhin, ON
    MENDELEEV COMMUNICATIONS, 2002, (01) : 28 - 30
  • [20] SYNTHESIS AND CHARACTERIZATION OF SOME NEW 2,6-DISUBSTITUTED THIAZOLO-[3,2-B][1,2,4]TRIAZINE-3,7-DIONES
    GIANNOLA, LI
    GIAMMONA, G
    PALAZZO, S
    LAMARTINA, L
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (12): : 2707 - 2710