Eco-friendly C-3 Selenation of Imidazo[1,2-a]pyridines in Ionic Liquid

被引:14
|
作者
Wang, Xin [1 ]
Mu, Shiqiang [1 ]
Sun, Ting [1 ]
Sun, Kai [1 ]
机构
[1] Anyang Normal Univ, Coll Chem & Chem Engn, Anyang 455000, Peoples R China
基金
中国国家自然科学基金;
关键词
selenation; imidazo[1,2-a]pyridines; C-3; functionalization; electrophilic mechanism; DIRECT ARYLATION; SELENIUM POWDER; IMIDAZOHETEROCYCLES; SULFENYLATION; EFFICIENT; CATALYST; ORGANOSELENIUM; CHALCOGENATION; THIOCYANATION; BROMIDES;
D O I
10.6023/cjoc201904057
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An relative eco-friendly protocol for the direct C-3 selenation of imidazo[1,2-a]pyridines with vorious organoselenides has been developed, gaving the desired products in moderate to excellent yields. Preliminary experimental results are consistent with a C-3 electrophilic functionalization mechanism. The features with relative green reaction conditions, broad substrate scope, and easy scale-up operation would make this strategy promising and important for the preparation of nitrogen and selenium containing molecules.
引用
收藏
页码:2802 / 2807
页数:6
相关论文
共 52 条
  • [41] Peroxodisulfate-mediated selenoamination of alkenes yielding amidoselenide-containing sulfamides and azoles
    Sun, Kai
    Wang, Xin
    Lv, Yunhe
    Li, Gang
    Jiao, Hezhen
    Dai, Changwei
    Li, Yangyang
    Zhang, Chong
    Liu, Lin
    [J]. CHEMICAL COMMUNICATIONS, 2016, 52 (54) : 8471 - 8474
  • [42] Copper-Catalyzed Selenylation of Imidazo[1,2-a]pyridines with Selenium Powder via a Radical Pathway
    Sun, Pengfei
    Jiang, Min
    Wei, Wei
    Min, Yuanyuan
    Zhang, Wen
    Li, Wanhui
    Yang, Daoshan
    Wang, Hua
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (06): : 2906 - 2913
  • [43] Catalytic C-H arylation of SEM-protected azoles with palladium complexes of NHCs and phosphines
    Touré, BB
    Lane, BS
    Sames, D
    [J]. ORGANIC LETTERS, 2006, 8 (10) : 1979 - 1982
  • [44] Natural Deep Eutectic Solvent-Catalyzed Selenocyanation of Activated Alkynes via an Intermolecular H-Bonding Activation Process
    Wu, Chao
    Xiao, Hai-Jing
    Wang, Shu-Wen
    Tang, Man-Sheng
    Tang, Zi-Long
    Xia, Wen
    Li, Wen-Feng
    Cao, Zhong
    He, Wei-Min
    [J]. ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2019, 7 (02): : 2169 - 2175
  • [45] Ultrasound-promoted Bronsted acid ionic liquid-catalyzed hydrothiocyanation of activated alkynes under minimal solvent conditions
    Wu, Chao
    Lu, Ling-Hui
    Peng, Ai-Zhong
    Jia, Guo-Kai
    Peng, Cun
    Cao, Zhong
    Tang, Zilong
    He, Wei-Min
    Xu, Xinhua
    [J]. GREEN CHEMISTRY, 2018, 20 (16) : 3683 - 3688
  • [46] 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
    [J]. SCIENCE CHINA-CHEMISTRY, 2019, 62 (04) : 460 - 464
  • [47] Bronsted Acidic Ionic Liquid-Promoted Amidation of Quinoline N-Oxides with Nitriles
    Xie, Long-Yong
    Peng, Sha
    Lu, Ling-Hui
    Hu, Jue
    Bao, Wen-Hu
    Zeng, Fei
    Tang, Zilong
    Xu, Xinhua
    He, Wei-Min
    [J]. ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2018, 6 (06): : 7989 - 7994
  • [48] Catalyst-Free Regioselective C-3 Thiocyanation of Imidazopyridines
    Yang, Daoshan
    Yan, Kelu
    Wei, Wei
    Li, Guoqing
    Lu, Shenglei
    Zhao, Caixia
    Tian, Laijin
    Wang, Hua
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (21): : 11073 - 11079
  • [49] Ionic Liquid from Vitamin B1 Analogue and Heteropolyacid: A Recyclable Heterogeneous Catalyst for Dehydrative Coupling in Organic Carbonate
    Yang, Guo-Ping
    Wu, Xun
    Yu, Bing
    Hu, Chang-Wen
    [J]. ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2019, 7 (04) : 3727 - +
  • [50] Ruthenium-catalyzed direct C-3 oxidative olefination of imidazo[1,2-a]pyridines
    Zhan, Haiying
    Zhao, Limin
    Li, Naiying
    Chen, Longbin
    Liu, Jingyun
    Liao, Jinqiang
    Cao, Hua
    [J]. RSC ADVANCES, 2014, 4 (60): : 32013 - 32016