Facile Synthesis of Hydrazine Derivatives of 5H-Pyrrolo[3,4-b]pyrazine and 1H-Pyrrolo[3,4-b]quinoxaline

被引:6
|
作者
Hordiyenko, Olga V. [1 ]
Rudenko, Igor V. [1 ]
Zamkova, Irina A. [1 ]
Denisenko, Oleksandr V. [1 ]
Biitseva, Angelina V. [1 ]
Arrault, Axelle [2 ]
Tolmachev, Andrei A. [1 ]
机构
[1] Taras Shevchenko Natl Univ Kyiv, UA-01601 Kiev, Ukraine
[2] ENSIC, INPL, Lab Chim Phys Macromol, F-54001 Nancy, France
来源
SYNTHESIS-STUTTGART | 2013年 / 45卷 / 24期
关键词
heterocycles; nitriles; cyclization; chemoselectivity; hydrazones; HYDROGEN-CYANIDE CHEMISTRY; EXCITED-STATE; COMPLEXES; DIIMINOSUCCINONITRILE; DIAMINOMALEONITRILE; QUINOXALINES;
D O I
10.1055/s-0033-1340042
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient and efficient route for the chemoselective synthesis of carbohydrazide, arenesulfonylhydrazide, and thiosemicarbazone derivatives of 5H-pyrrolo[3,4-b]pyrazine and 1H-pyrrolo[3,4-b]quinoxaline from the corresponding dinitriles and substituted hydrazines was elaborated. The synthesis of starting pyrazine-2,3-dicarbonitrile was sufficiently improved by using concentrated HCl as a catalyst.
引用
收藏
页码:3375 / 3382
页数:8
相关论文
共 50 条
  • [11] Photophysical properties of derivatives of 1H-pyrazolo[3,4-b]quinoline and 1H-pyrazolo[3,4-b]quinoxaline
    Mac, M.
    Uchacz, T.
    Andrzejak, M.
    Dane, A.
    Szlachcic, P.
    Nowak, P.
    POLISH JOURNAL OF CHEMISTRY, 2007, 81 (04) : 557 - 572
  • [12] REACTIONS OF 4-ARYLMETHYLENEPYRROLIDINE-2,3-DIONES - SYNTHESIS OF PYRROLO[3,4-B]-PYRIDINES AND PYRROLO[3,4-B]-QUINOLINES
    MADHAV, R
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (18): : 2108 - 2110
  • [13] Convenient synthesis of functionalized pyrrolo[3,4-b]pyridines and pyrrolo[3,4-b]quinolines via three-component reactions
    Jiang, Yan-Hong
    Xiao, Man
    Yan, Chao-Guo
    RSC ADVANCES, 2016, 6 (42) : 35609 - 35616
  • [14] Efficient synthesis of pyrrolo[3,4-b]hexahydro-1H-1,5-benzodiazepine derivatives
    Zaleska, B
    Ciez, D
    Lech, J
    SYNLETT, 2001, (12) : 1953 - 1955
  • [15] SYNTHESIS OF SOME PYRROLO [3,4-B] QUINOXALINE 4,9-DIOXIDES
    HADDADIN, MJ
    ATFAH, MA
    HETEROCYCLES, 1981, 16 (02) : 251 - 256
  • [16] SYNTHESIS OF COMPOUNDS IN THE PYRROLO[3,4-B]INDOLE SERIES
    SOUTHWICK, PL
    OWELLEN, RJ
    JOURNAL OF ORGANIC CHEMISTRY, 1960, 25 (07): : 1133 - 1138
  • [17] SYNTHESIS OF FURAZANO[3,4-B]-PYRAZINE DERIVATIVES
    YEREMEYEV, AV
    ANDRIANOV, VG
    PISKUNOVA, IP
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1978, (05): : 613 - 615
  • [18] Synthesis of 1H-thieno[3,4-c]pyrazoles, thieno[3,4-b]furans, selenolo[3,4-b]furans and pyrrolo[3,4-d]thiazoles
    Shafiee, A
    Ebrahimzadeh, MA
    Shahbazi, J
    Hamedpanah, S
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1998, 35 (01) : 71 - 75
  • [19] SYNTHESIS AND PHARMACOLOGICAL STUDY OF PYRROLO[3,4-B]BENZO[1,5]DIAZEPINE DERIVATIVES
    SOROKINA, IK
    ALEKSEYEVA, LM
    PARSHIN, VA
    ASNINA, VV
    YUZHAKOV, SD
    PARIMBETOVA, RB
    GRANIK, VG
    KHIMIKO-FARMATSEVTICHESKII ZHURNAL, 1991, 25 (11): : 16 - 18
  • [20] REACTIONS OF IH-PYRROLO(3,4-B)QUINOLINE DERIVATIVES
    TANAKA, T
    MASHIMO, K
    WAGATSUM.M
    TETRAHEDRON LETTERS, 1971, (30) : 2803 - &