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
  • [31] Synthesis of novel building blocks of 1H-pyrrolo[3,4-b]quinolin-3(2H)-one and evaluation of their antitumor activity
    Lingaiah Nagarapua
    Hanmant K. Gaikwad
    Sheeba Rani Manikonda
    Rajashaker Bantu
    Krishna Madhuri Manda
    Shasi Vardhan Kalivendi
    Medicinal Chemistry Research, 2013, 22 : 165 - 174
  • [32] NITRATION OF 1H-PYRAZOLO(3,4-B)QUINOXALINE
    KOHLSTOCK, B
    HENSEKE, G
    ZEITSCHRIFT FUR CHEMIE, 1972, 12 (10): : 385 - +
  • [33] Synthesis of fluorinated furo- and pyrrolo[3,4-b]quinoxaline 4,9-dioxides
    Kotovskaya, SK
    Perova, NM
    Charushin, VN
    Chupakhin, ON
    MENDELEEV COMMUNICATIONS, 1999, (02) : 76 - 77
  • [34] Synthesis, photoluminescence and electroluminescence of new 1H-pyrazolo[3,4-b]quinoxaline derivatives
    Wang, PF
    Xie, ZY
    Hong, ZR
    Tang, JX
    Wong, OY
    Lee, CS
    Wong, NB
    Lee, ST
    JOURNAL OF MATERIALS CHEMISTRY, 2003, 13 (08) : 1894 - 1899
  • [35] SYNTHESIS AND REACTIONS OF 1H-PYRAZOLO(3,4-B)QUINOXALINE (FLAVAZOLE)
    SAUER, W
    HENSEKE, G
    ZEITSCHRIFT FUR CHEMIE, 1970, 10 (10): : 381 - &
  • [36] PREPARATION OF DERIVATIVES OF 9-OXO-2,3,4,9-TETRAHYDRO-1H-PYRROLO[3,4-B] QUINOLINE AND 7-OXO-7,9,10,11-TETRAHYDRO-8H-BENZO[H] PYRROLO[3,4-B] QUINOLINE
    MADHAV, R
    DUFRESNE, RF
    SOUTHWIC.PL
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1973, 10 (02) : 225 - 228
  • [37] A facile synthesis and antibacterial activity of novel pyrrolo[3,4-b]quinolin-2(3H)-yl)benzamides
    Largani, Tahere Hosseyni
    Imanzadeh, Gholamhassan
    Zahri, Saber
    Pesyan, Nader Noroozi
    Sahin, Ertan
    GREEN CHEMISTRY LETTERS AND REVIEWS, 2017, 10 (04) : 387 - 392
  • [38] Synthesis, Biological Evaluation and Docking Studies of Functionalized Pyrrolo[3,4-b]pyridine Derivatives
    Saigal
    Ghanem, Younes S. A.
    Uddin, Amad
    Khan, Sarfaraz
    Abid, Mohammad
    Khan, Md. Musawwer
    CHEMISTRYSELECT, 2021, 6 (09): : 2323 - 2334
  • [39] NICETHAMIDE ANALOGS .7. SYNTHESIS OF A PYRROLO [3,4-B]- AND PYRROLO [3,4-C]PYRIDINONE AS NICETHAMIDE ANALOGS
    SATTLER, HJ
    SCHUNACK, W
    CHEMISCHE BERICHTE-RECUEIL, 1975, 108 (04): : 1003 - 1009
  • [40] Synthesis of some new pyrrolo[3,4-b][1,5]benzodiazepines of pharmaceutical interest
    Sofan, MA
    PHARMAZIE, 1996, 51 (08): : 548 - 550