A Beckmann rearrangement initiated by trifluoromethanesulfonic anhydride in the synthesis of compounds containing a new pyrazolo[3',4':5,6]pyrido[3,2-b]azepine heterocyclic system

被引：0
|
作者：
Georgiy G. Yakovenko
Marta S. Yagodkina-Yakovenko
Sergey Yu. Suykov
Mikhailo V. Vovk
机构：
[1] National University “Kyiv-Mohyla Academy”,
[2] Institute of Organic Chemistry,undefined
[3] National Academy of Sciences of Ukraine,undefined
[4] Enamine Ltd.,undefined
来源：
Chemistry of Heterocyclic Compounds | 2021年 / 57卷
关键词：
1,3-cyclohexanediones; pyrazolopyridoazepines; pyrazolo[4,3-; ]quinolin-8-ones; trifluoromethanesulfonic anhydride; Beckmann rearrangement;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
N-Boc-5-formylpyrazol-4-amines reacted with 1,3-cyclohexanediones in AcOH–1,4-dioxane medium in the presence of pyrrolidine, resulting in the formation of pyrazolo[4,3-b]quinolin-8-one derivatives that were converted into the respective oximes. A reaction of the latter with trifluoromethanesulfonic anhydride under mild conditions was used to synthesize hexahydropyrazolo[3',4':5,6]pyrido[3,2-b]-azepin-4-ium trifluoromethanesulfonates.
引用
收藏
页码：199 / 206
页数：7
相关论文
共 50 条
  • [1] A Beckmann rearrangement initiated by trifluoromethanesulfonic anhydride in the synthesis of compounds containing a new pyrazolo[3′,4′:5,6]pyrido[3,2-b]azepine heterocyclic system
    Yakovenko, Georgiy G.
    Yagodkina-Yakovenko, Marta S.
    Suykov, Sergey Yu.
    Vovk, Mikhailo V.
    [J]. CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2021, 57 (02) : 199 - 206
  • [2] Synthesis of derivatives of the new heterocyclic system pyrimido[5',4':5,6]pyrido[3,2-b]indole
    Ryabova, S. Yu.
    Alekseeva, L. M.
    Masterova, N. S.
    Granik, V. G.
    [J]. RUSSIAN CHEMICAL BULLETIN, 2007, 56 (08) : 1588 - 1594
  • [3] Synthesis of derivatives of the new heterocyclic system pyrimido[5′,4′:5,6]pyrido[3,2-b]indole
    S. Yu. Ryabova
    L. M. Alekseeva
    N. S. Masterova
    V. G. Granik
    [J]. Russian Chemical Bulletin, 2007, 56 : 1588 - 1594
  • [4] Synthesis of 1,4,5,6-tetrahydropyrazolo[3,4-d]pyrido[3,2-b]azepine
    Albright, JD
    Du, XM
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2000, 37 (01) : 41 - 46
  • [5] Synthesis of pyrazolo-annelated heterocyclic ring compounds such as pyrazolo[3,4-b]pyridines and pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidines
    Jachak, Madhukar N.
    Avhale, Appasaheb B.
    Toche, Ragunath B.
    Sabnis, Ram W.
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2007, 44 (02) : 343 - 347
  • [6] Synthesis of novel pyrido[3′,2′:5,6]thiopyrano[3,2-b]indol-5(6H)-ones and 6H-pyrido[3′,2′:5,6]thiopyrano[4,3-b]quinolines, two new heterocyclic ring systems
    Da Settimo, A
    Marini, AM
    Primofiore, G
    Da Settimo, F
    Salerno, S
    Simorini, F
    Pardi, G
    La Motta, C
    Bertini, D
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2002, 39 (05) : 1001 - 1006
  • [7] Alkylation of pyrimido[5′,4′:5,6]pyrido[3,2-b]indol-4-one derivatives
    N. S. Masterova
    L. M. Alekseeva
    A. S. Shashkov
    V. A. Tafeenko
    S. Yu. Ryabova
    V. G. Granik
    [J]. Russian Chemical Bulletin, 2008, 57 : 1765 - 1772
  • [8] Alkylation of pyrimido[5′,4′:5,6]pyrido[3,2-b]indol-4-one derivatives
    Masterova, N. S.
    Alekseeva, L. M.
    Shashkov, A. S.
    Tafeenko, V. A.
    Ryabova, S. Yu.
    Granik, V. G.
    [J]. RUSSIAN CHEMICAL BULLETIN, 2008, 57 (08) : 1765 - 1772
  • [9] A NEW SYNTHESIS OF PYRIDO[3,2-B][1,4]BENZOTHIAZINES
    MCCARTHY, ET
    TYNDALL, DV
    MEEGAN, MJ
    [J]. JOURNAL OF CHEMICAL RESEARCH-S, 1988, (05): : 145 - 145
  • [10] HETEROCYCLIC-SYSTEMS CONTAINING BRIDGEHEAD NITROGEN ATOM - FACILE SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF THIAZOLO[3,2-B]-S-TETRAZINES AND PYRAZOLO[3',4'-4,5]THIAZOLO[3,2-B]-S-TETRAZINES - A NOVEL HETEROCYCLIC SYSTEM
    MOHAN, J
    KIRAN
    DUREJA, P
    [J]. INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1990, 29 (02): : 148 - 151
12345