I2/TBPB Mediated Oxidative Reaction to Construct of Imidazo[1,5-α]pyridines under Metal-Free Conditions

被引:10
作者
Qin, Mingda [1 ]
Tian, Yuan [1 ]
Guo, Xin [1 ]
Yuan, Xinglong [1 ]
Yang, Xueying [1 ]
Chen, Baohua [1 ,2 ]
机构
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China
[2] Lanzhou Univ, Zhongwei High Tech Inst, Zhongwei 755500, Ningxia, Peoples R China
基金
中国国家自然科学基金;
关键词
cycloaddition; heterocycles; high atom efficiency; metal-free catalysis; new reaction; SELECTIVE 3+2 CYCLOADDITION; PYRIDINE N-OXIDE; C-C BOND; EFFICIENT SYNTHESIS; 1,3-DIPOLAR CYCLOADDITION; C(SP(3))-H BONDS; AMINATION; DERIVATIVES; 1,2,4-TRIAZOLES; HETEROCYCLES;
D O I
10.1002/ajoc.201800285
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new method for the synthesis of imidazo[1,5-alpha]pyridines, one of the most important N-heterocyclic compounds due to their wide application, was reported in this study. Specifically, using I-2 as a non-metal catalyst and TBPB as an oxidant can efficiently facilitate the synthesis and avoid the use of a metal catalyst. The reaction between ethyl (E)-2-(benzylideneamino)acetate and pyridine represents an unprecedented 1,3-diolar cycloaddition in highly straightforward process with great value.
引用
收藏
页码:1591 / 1594
页数:4
相关论文
共 50 条
  • [21] Electrochemical synthesis of selenocyanated imidazo[1,5-a]quinolines under metal catalyst- and chemical oxidant-free conditions
    Zhang, Jinjin
    Wang, Huiqiao
    Chen, Yaru
    Xie, Haiquan
    Ding, Chenghua
    Tan, Jiajing
    Xu, Kun
    [J]. CHINESE CHEMICAL LETTERS, 2020, 31 (06) : 1576 - 1579
  • [22] A Metal-Free Multicomponent Cascade Reaction for the Regiospecific Synthesis of 1,5-Disubstituted 1,2,3-Triazoles
    Cheng, Guolin
    Zeng, Xiaobao
    Shen, Jinhai
    Wang, Xuesong
    Cui, Xiuling
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (50) : 13265 - 13268
  • [23] I2-promoted aerobic oxidative coupling of acetophenes with amines under metal-free conditions: facile access to α-ketoamides
    Guo, Shiyu
    Fang, Zheng
    Yang, Zhao
    Liu, Chengkou
    Dai, Zhongxue
    Zhao, Lihuan
    Guo, Kai
    [J]. RSC ADVANCES, 2016, 6 (02): : 1503 - 1507
  • [24] I2-mediated amination/cyclization of ketones with 2-aminopyridines under high-speed ball milling: solvent- and metal-free synthesis of 2,3-substituted imidazo[1,2-a]pyridines and zolimidine
    Wang, Fang-Jian
    Xu, Hui
    Xin, Ming
    Zhang, Ze
    [J]. MOLECULAR DIVERSITY, 2016, 20 (03) : 659 - 666
  • [25] Metal-Free, H2O2-Mediated, Regioselective Direct C-3 Hydroxylation of Imidazo[1,2-a]pyridines via C(sp2)-H Bond Functionalization
    Yadav, Ravi Kant
    Kumar, Yogesh
    Chaudhary, Sandeep
    [J]. CHEMISTRYSELECT, 2020, 5 (29): : 9235 - 9239
  • [26] Metal- and base-free synthesis of imidazo[1,2-a]pyridines through elemental sulfur-initiated oxidative annulation of 2-aminopyridines and aldehydes
    Tan, Jing
    Ni, Penghui
    Huang, Huawen
    Deng, Guo-Jun
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (23) : 4227 - 4230
  • [27] Heterogeneously copper-catalyzed oxidative synthesis of imidazo[1,2-a]pyridines using 2-aminopyridines and ketones under ligand- and additive-free conditions
    Meng, Xu
    Wang, Yanmin
    Yu, Chaoying
    Zhao, Peiqing
    [J]. RSC ADVANCES, 2014, 4 (52) : 27301 - 27307
  • [28] Metal-free one-pot synthesis of 1,3-diazaheterocyclic compounds via I2-mediated oxidative C-N bond formation
    Tian, Xianhai
    Song, Lina
    Li, Ertong
    Wang, Qiang
    Yu, Wenquan
    Chang, Junbiao
    [J]. RSC ADVANCES, 2015, 5 (76) : 62194 - 62201
  • [29] Synthesis of imidazo[1,5-a]pyridines via I2-mediated sp3 C-H amination
    Hu, Zhiyuan
    Hou, Jiao
    Liu, Jie
    Yu, Wenquan
    Chang, Junbiao
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (31) : 5653 - 5660
  • [30] A Metal- and Azide-free Oxidative Coupling Reaction for the Synthesis of [1,2,3]Triazolo[1,5-a]quinolines and their Application to Construct C-C and C-P Bonds, 2-Cyclopropylquinolines and Imidazo[1,5-a]quinolines
    Shang, Zhi-Hao
    Zhang, Zhen-Xiao
    Weng, Wei-Zhao
    Wang, Yu-Fei
    Cheng, Tian-Wei
    Zhang, Qiu-Yi
    Song, Li-Qun
    Shao, Tian-Qi
    Liu, Kai-Xuan
    Zhu, Yan-Ping
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (02) : 490 - 496