Ga(ClO4)3-catalyzed Reaction of 1,2-Diamines and α-Bromoketones:Synthesis of 2-Substituted Quinoxalines

被引:0
|
作者
JI Yun-fei
机构
基金
中国国家自然科学基金;
关键词
Ga(ClO4)3; 1,2-Aryldiamine; α-Bromoketone; 2-Substituted quinoxaline; Solvent-free reaction;
D O I
暂无
中图分类号
O621.25 [];
学科分类号
摘要
Ga(ClO4)3-catalyzed reaction of 1,2-aryldiamines and α-bromoketones to afford 2-substituted quinoxalines in good yields is described.The reaction proceeded via grinding process with 10%(molar fraction) catalyst under solvent-free conditions at room temperature.For unsymmetrical o-phenylenediamines bearing electron-withdrawing groups,regio-selective quinoxalines were obtained.
引用
收藏
页码:642 / 646
页数:5
相关论文
共 50 条
  • [1] Ga(ClO4)3-catalyzed Reaction of 1,2-Diamines and α-Bromoketones: Synthesis of 2-Substituted Quinoxalines
    Ji Yun-fei
    Chen Tang-ming
    Mao Hai-feng
    Zou Jian-ping
    CHEMICAL RESEARCH IN CHINESE UNIVERSITIES, 2012, 28 (04) : 642 - 646
  • [2] Ga(ClO4)3-catalyzed synthesis of quinoxalines by cycloaddition of α-hydroxyketones and o-phenylenediamines
    Pan, Fan
    Chen, Tang-Ming
    Cao, Jia-Jia
    Zou, Jian-Ping
    Zhang, Wei
    TETRAHEDRON LETTERS, 2012, 53 (20) : 2508 - 2510
  • [3] First example of Cu(OTf)2-catalyzed synthesis of quinoxalines from α-diazoketones and aryl 1,2-diamines
    Yadav, J. S.
    Reddy, B. V. Subba
    Rao, Y. Gopala
    Narsaiah, A. V.
    CHEMISTRY LETTERS, 2008, 37 (03) : 348 - 349
  • [4] Multichannel Reaction of α-Bromoenones with 1,2-Diamines: Synthesis of 1,4-Diazabicyclo[4.1.0]hept-4-enes by Reaction with N-Unsubstituted 1,2-Diamines
    Muzalevskiy, Vasily M.
    Rulev, Alexander Yu.
    Kondrashov, Evgeniy V.
    Romanov, Alexey R.
    Ushakov, Igor A.
    Chertkov, Vyacheslav A.
    Nenajdenko, Valentine G.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (08) : 1612 - 1618
  • [5] An Effective Microwave-Induced Iodine-Catalyzed Method for the Synthesis of Quinoxalines via Condensation of 1,2-Diamines with 1,2-Dicarbonyl Compounds
    Bandyopadhyay, Debasish
    Mukherjee, Sanghamitra
    Rodriguez, Robert R.
    Banik, Bimal K.
    MOLECULES, 2010, 15 (06) : 4207 - 4212
  • [6] Practical synthesis of 3,3-substituted dihydroquinoxalin-2-ones from aryl 1,2-diamines using the Bargellini reaction
    Alanine, Thomas A.
    Stokes, Stephen
    Scott, James S.
    TETRAHEDRON LETTERS, 2016, 57 (39) : 4386 - 4388
  • [7] A NOVEL SYNTHESIS OF UNSYMMETRIC 1,2-DIAMINES FROM N-SUBSTITUTED 2-METHYLAZIRIDINES
    CHAMCHAANG, W
    PINHAS, AR
    JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (08): : 2531 - 2533
  • [8] FeCl3 AND MORPHOLINE AS EFFICIENT COCATALYSTS FOR THE ONE-STEP SYNTHESIS OF QUINOXALINES FROM α-HYDROXYKETONES AND 1,2-DIAMINES
    Song, Weibin
    Liu, Peng
    Lei, Min
    You, Hanyun
    Chen, Xubing
    Chen, Hu
    Ma, Lei
    Hu, Lihong
    SYNTHETIC COMMUNICATIONS, 2012, 42 (02) : 236 - 245
  • [9] Sc(OTf)3-Catalyzed C-C Bond Cleavage of Unactivated Acylazaarenes with 1,2-Diamines to Afford Azaarenes and Imidazoles
    Pang, Bo
    Xin, Hai-Long
    Choi, Jeesoo
    Morimoto, Hiroyuki
    Ohshima, Takashi
    ORGANIC LETTERS, 2025, 27 (09) : 2075 - 2080
  • [10] Reaction of 1,2-diamines with 4-hydroxycoumarin. Synthesis of 1,4-diazepin-5-ones
    Hamdi, M
    Cottet, S
    Tedeschi, C
    Speziale, V
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1997, 34 (06) : 1821 - 1824