2-[(3,5-Diamino-1H-pyrazol-4-yl)methylidene]-1,2-dihydro-3H-indol-3-ones: synthesis and properties

被引:2
|
作者
Masterova, N. S. [1 ]
Ryabova, S. Yu. [1 ]
Alekseeva, L. M. [1 ]
Shashkov, A. S. [2 ]
Chernyshev, V. V. [3 ]
Granik, V. G. [1 ]
机构
[1] State Res Ctr Antibiot, Moscow 117003, Russia
[2] Russian Acad Sci, ND Zelinskii Organ Chem Inst, Moscow 119991, Russia
[3] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119899, Russia
关键词
3-acetoxy-2-(2,2-dicyanovinyl)indole; hydrazines; 2-[(3,5-diamino-1H-pyrazol-4-yl)methylidene]indolin-3-ones; acetylation; X-ray diffraction analysis; DMF and DMAA dimethyl acetals; cyclization; pyrazolo[4 ',3 ':5,6]pyrido[3,2-b]indole; POWDER DIFFRACTION; DERIVATIVES; RELIABILITY; PYRIMIDINE; CRITERION; NITRILES; PROGRAM;
D O I
10.1007/s11172-009-0269-y
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Reactions of 3-acetoxy-2-(2,2-dicyanovinyl)indole with hydrazine hydrate and methyl-and phenylhydrazines afforded new indolin-3-one derivatives, namely, 2-[( 3,5-diaminopyrazol-4-yl)methylidene]indolin-3-ones. Reactions of the compounds obtained with acetic anhydride and DMF and DMAA dimethyl acetals were studied. Cyclization of 2-[(3,5-diamino-1H-pyrazol-4-yl)methylidene]-1,2-dihydro-3H-indolinone gave 3-amino-1,5-dihydropyrazolo-[4',3' : 5,6]pyrido[3,2-b]indole, a representative of a novel heterocyclic system.
引用
收藏
页码:1973 / 1980
页数:8
相关论文
共 50 条
  • [31] (E)-2-[(3-Methyl-5-phenoxy-1-phenyl-1H-pyrazol-4-yl) methylidene]hydrazinecarbothioamide
    Fun, Hoong-Kun
    Quah, Ching Kheng
    Shetty, Shobhitha
    Kalluraya, Balakrishna
    Nitinchandra
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O2146 - +
  • [32] 2-(1H-Indol-3-yl)acetohydrazide
    Sidra, Lala Rukh
    Khan, Islam Ullah
    Yar, Muhammad
    Simpson, Jim
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O3140 - +
  • [33] 2-(4-Methoxy-1H-indol-3-yl)acetonitrile
    Lu, Yong-Hong
    Pan, Mei-Ling
    Luo, Yang-Hui
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2012, 68
  • [34] 2-(4-Bromo-1H-indol-3-yl)acetonitrile
    Mao, Qiu-Xia
    Zhang, Chen-Guang
    Li, Jin-Feng
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2012, 68 : O451 - U1075
  • [35] 2-(4-Chloro-1H-indol-3-yl)acetonitrile
    Pan, Mei-Ling
    Li, Xiang
    Luo, Yang-Hui
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2012, 68
  • [36] Synthesis and Antibacterial Activity of 2-(4,5-Dihydro-3-substituted-1H-pyrazol-5-yl)-3-methoxyquinoxalines
    Devi, T. Rajani
    Laxminarayana, E.
    Giri, T.
    Chary, M. Thirumala
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2020, 30 (03) : 381 - 385
  • [37] Synthesis of 1-[2-(1H-Indol-3-yl)ethyl]-4-acetyl-3-hydroxy-5-phenyl-1H-pyrrol-2(5H)-ones
    Nasakin, O. E.
    Kazantseva, M. I.
    Varkentin, L. I.
    Gein, V. L.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2018, 88 (06) : 1270 - 1272
  • [38] Synthesis of 1-[2-(1H-Indol-3-yl)ethyl]-4-acetyl-3-hydroxy-5-phenyl-1H-pyrrol-2(5H)-ones
    O. E. Nasakin
    M. I. Kazantseva
    L. I. Varkentin
    V. L. Gein
    Russian Journal of General Chemistry, 2018, 88 : 1270 - 1272
  • [39] Novel regiospecific method for synthesis of 2-(3,5-Diaryl-4,5-dihydro-1H-pyrazol-1-yl)-4,6-diarylpyrimidines
    Bairwa, Ranjeet
    Degani, Mariam S.
    SYNTHETIC COMMUNICATIONS, 2008, 38 (06) : 943 - 952
  • [40] (3,5-Dimethyl-1H-pyrazol-1-yl){3-[(3,5dimethyl-1H-pyrazol-1-yl) carbonyl]-5methylindolizin-1-yl}methanone
    Song, Xiang-Yun
    Gu, Wei-Jin
    Jiang, Yu-Liang
    Wang, Bing-Xiang
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O450 - +