Transition Metal-Free Iodosobenzene-Promoted Direct Oxidative 3-Arylation of Quinoxalin-2(H)-ones with Arylhydrazines

被引:145
作者
Paul, Sanjay [1 ]
Ha, Ji Hyeon [1 ]
Park, Ga Eul [1 ]
Lee, Yong Rok [1 ]
机构
[1] Yeungnam Univ, Sch Chem Engn, Gyongsan 712749, South Korea
基金
新加坡国家研究基金会;
关键词
arylhydrazines; benzo[g]quinoxalinones; iodosylbenzene (PHIO)-promoted reaction; pyrido[3; 4-b]pyrazinones; transition metal-free oxidative arylation; ALDOSE REDUCTASE INHIBITORS; TERT-BUTYL HYDROPEROXIDE; QUINOXALINONE DERIVATIVES; POLYVALENT IODINE; DIRECT ARYLATION; BOND FORMATION; QUINOXALIN-2(1H)-ONES; CHEMISTRY; ENAMINES; CYCLIZATION;
D O I
10.1002/adsc.201700070
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A transition metal-free iodosobenzene-promoted direct oxidative 3-arylation of quinoxalin-2(H)-ones was developed using various arylhydrazines under air. The protocol affords a variety of 3-arylquinoxalin-2(H)-one derivatives in moderate to good yields. This method provides a rapid access to biologically interesting benzo[g]quinoxalinones and pyrido[3,4-b]pyrazinones. The present methodology features high functional group tolerance including base-sensitive groups as well as allyl- and benzyl-substituted quinoxalin-2(H)-ones under mild reaction conditions.
引用
收藏
页码:1515 / 1521
页数:7
相关论文
共 50 条
  • [1] Transition Metal-Free Direct C-3 Arylation of Quinoxalin-2(1H)-ones with Arylamines under Mild Conditions
    Yuan, Jinwei
    Liu, Shuainan
    Qu, Lingbo
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (23) : 4197 - 4207
  • [2] Direct decarboxylative C-H 3-arylation of quinoxalin-2(H)-ones with aryl acyl peroxides leading to 3-arylquinoxalin-2(1H)-ones
    Lv, Yufen
    Bao, Pengli
    Yue, Huilan
    Wei, Wei
    TETRAHEDRON LETTERS, 2020, 61 (47)
  • [3] Metal-Free C3 Hydroxylation of Quinoxalin-2(1H)-ones in Water
    Peng, Sha
    Hu, Die
    Hu, Jia-Li
    Lin, Ying-Wu
    Tang, Shan-Shan
    Tang, Hai-Shan
    He, Jun-Yi
    Cao, Zhong
    He, Wei-Min
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (24) : 5721 - 5726
  • [4] Transition-metal free direct C-H functionalization of quinoxalin-2(1H)-ones with oxamic acids leading to 3-carbamoyl quinoxalin-2(1H)-ones
    Yuan, Jin-Wei
    Zhu, Jun-Liang
    Zhu, Hu-Lin
    Peng, Fang
    Yang, Liang-Yu
    Mao, Pu
    Zhang, Shou-Ren
    Li, Yan-Chun
    Qu, Ling-Bo
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (02): : 273 - 285
  • [5] Transition-metal-free direct C-3 alkylation of quinoxalin-2(1H)-ones with ethers
    Yuan, Jinwei
    Fu, Junhao
    Yin, Jihong
    Dong, Zhenhua
    Xiao, Yongmei
    Mao, Pu
    Qu, Lingbo
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (19): : 2820 - 2828
  • [6] Metal-free C3-alkoxycarbonylation of quinoxalin-2(1H)-ones with carbazates as ecofriendly ester sources
    Xie, Long-Yong
    Peng, Sha
    Fan, Tai-Gang
    Liu, Yan-Fang
    Sun, Meng
    Jiang, Li-Lin
    Wang, Xing-Xing
    Cao, Zhong
    He, Wei-Min
    SCIENCE CHINA-CHEMISTRY, 2019, 62 (04) : 460 - 464
  • [7] Metal-free regioselective nitration of quinoxalin-2(1H)-ones with tert-butyl nitrite
    Li, Yi-Na
    Li, Xue-Lin
    Wu, Jin-Bo
    Jiang, Hong
    Liu, Yunmei
    Guo, Yu
    Zeng, Yao-Fu
    Wang, Zhen
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (48) : 10554 - 10559
  • [8] Photocatalyst-free Photoredox Arylation of Quinoxalin-2(1H)-Ones with Aryldiazo Sulfones
    Jung, Hye Im
    Lee, Ju Hui
    Kim, Dae Young
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2018, 39 (08): : 1003 - 1006
  • [9] Metal-free visible-light-initiated direct C3 alkylation of quinoxalin-2(1H)-ones and coumarins with unactivated alkyl iodides
    Sun, Jun
    Yang, Hua
    Zhang, Bo
    GREEN CHEMISTRY, 2022, 24 (02) : 858 - 863
  • [10] Metal-free three-component cyanoalkylation of quinoxalin-2(1H)-ones with vinylarenes and azobis(alkylcarbonitrile)s
    Bhuyan, Mayurakhi
    Sharma, Suraj
    Baishya, Gakul
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (07) : 1462 - 1474