Synthesis of functionalized imidazo[4,5-e]thiazolo[3,2-b]tri-azines by condensation of imidazo[4,5-e]triazinethiones with DMAD or DEAD and rearrangement to imidazo[4,5-e]thiazolo[2,3-c]triazines

被引：10
|
作者：
Izmest'ev, Alexei N. [1 ,2 ]
Vinogradov, Dmitry B. [1 ]
Kolotyrkina, Natalya G. [1 ]
Kravchenko, Angelina N. [1 ,3 ]
Gazieva, Galina A. [1 ]
机构：
[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Leninsky Prosp 47, Moscow 119991, Russia
[2] Natl Univ Sci & Technol MISiS, 4 Leninsky Prosp, Moscow 119049, Russia
[3] Plekhanov Russian Univ Econ, 36 Stremyanny Lane, Moscow 117997, Russia
来源：
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 17卷
关键词：
amidine rearrangement; cyclocondensation; heterocycles; thiazolidine-4-one; 1; 2; 4-triazine; BIOLOGICAL-ACTIVITY; DERIVATIVES; THIAZOLIDIN-4-ONE;
D O I：
10.3762/bjoc.17.87
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Two series of functionalized imidazothiazolotriazine derivatives were synthesized via the condensation of imidazo[4,5-e]-1,2,4-triazine-3-thiones with acetylenedicarboxylic acid dimethyl and diethyl esters (DMAD and DEAD) and subsequent base-catalyzed rearrangement of the obtained imidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazines into regioisomeric imidazo[4,5-e]thiazolo[2,3-c]-1,2,4-triazine derivatives.
引用
收藏
页码：1141 / 1148
页数：8
相关论文
共 50 条
  • [1] Synthesis of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines via a base-induced rearrangement of functionalized imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazines
    Vinogradov, Dmitry B.
    Izmest'ev, Alexei N.
    Kravchenko, Angelina N.
    Strelenko, Yuri A.
    Gazieva, Galina A.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2023, 19 : 1047 - 1054
  • [2] Synthesis of imidazo[4,5-e][1,3]thiazolo-[3,2-b][1,2,4]triazines
    Gazieva, G. A.
    Poluboyarov, P. A.
    Nelyubina, Yu. V.
    Struchkova, M. I.
    Kravchenko, A. N.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2012, 48 (09) : 1382 - 1389
  • [3] Synthesis of imidazo[4,5-e][1,3]thiazolo-[3,2-b][1,2,4]triazines
    G. A. Gazieva
    P. A. Poluboyarov
    Yu. V. Nelyubina
    M. I. Struchkova
    A. N. Kravchenko
    Chemistry of Heterocyclic Compounds, 2012, 48 : 1382 - 1389
  • [4] Synthesis of imidazo[4,5-e]thiazolo[2,3-c]-1,2,4-triazine-2,8-diones via a rearrangement of imidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine-2,7-diones in the reaction with isatins
    Gazieva, Galina A.
    Izmest'ev, Alexei N.
    Nelyubina, Yulia V.
    Kolotyrkina, Natalya G.
    Zanin, Igor E.
    Kravchenko, Angelina N.
    RSC ADVANCES, 2015, 5 (55): : 43990 - 44002
  • [5] 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
  • [6] Cascade synthesis of the first imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazine derivative
    Kravchenko, Angelina N.
    Gazieva, Galina A.
    Vasilevskii, Sergei V.
    Nelyubina, Yulia V.
    MENDELEEV COMMUNICATIONS, 2014, 24 (02) : 119 - 121
  • [7] Synthesis and biological activity of oxindolylidene derivatives of imidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazin-7-ones and imidazo[4,5-e]thiazolo[2,3-с]-1,2,4-triazin-8-ones
    A. N. Izmest’ev
    G. A. Gazieva
    A. S. Kulikov
    L. V. Anikina
    N. G. Kolotyrkina
    A. N. Kravchenko
    Russian Journal of Organic Chemistry, 2017, 53 : 753 - 763
  • [8] Synthesis and biological activity of oxindolylidene derivatives of imidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazin-7-ones and imidazo[4,5-e]thiazolo[2,3-N]-1,2,4-triazin-8-ones
    Izmest'ev, A. N.
    Gazieva, G. A.
    Kulikov, A. S.
    Anikina, L. V.
    Kolotyrkina, N. G.
    Kravchenko, A. N.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 53 (05) : 753 - 763
  • [9] 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
    Izmest'ev, Alexei N.
    Vasileva, Darya A.
    Melnikova, Elizaveta K.
    Kolotyrkina, Natalya G.
    Borisova, Irina A.
    Kravchenko, Angelina N.
    Gazieva, Galina A.
    NEW JOURNAL OF CHEMISTRY, 2019, 43 (02) : 1038 - 1052
  • [10] 6-AZAPURINES (IMIDAZO[4,5-E]-AS-TRIAZINES)
    YONEDA, F
    NAGAMURA, T
    KAWAMURA, M
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (16) : 658 - 659
12345