Switching the regioselectivity in the copper-catalyzed synthesis of iodoimidazo[1,2-a]pyridines

被引:43
|
作者
Samanta, Sadhanendu [1 ]
Jana, Sourav [1 ]
Mondal, Susmita [1 ]
Monir, Kamarul [1 ]
Chandra, Swapan K. [1 ]
Hajra, Alakananda [1 ]
机构
[1] Visva Bharati, Dept Chem, Santini Ketan 731235, W Bengal, India
关键词
ONE-POT SYNTHESIS; OXIDATIVE CYCLIZATION; COUPLING REACTION; IMIDAZOHETEROCYCLES; TRIFLUOROMETHYLATION; 2-AMINOPYRIDINE; NITROOLEFINS; CONSTRUCTION; DIAMINATION; ANNULATION;
D O I
10.1039/c6ob00656f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A unique copper-catalyzed binucleophilic switching of 2-aminopyridine has been developed for the regioselective synthesis of 2- and 3-iodoimidazo[1,2-a]pyridines using alkenes/alkynes as coupling partners in the presence of molecular iodine under aerobic reaction conditions. This method was also applied to the synthesis of 2-iodo-3-phenylbenzo[d]imidazo[2,1-b]thiazoles. This protocol offers an easy route towards the synthesis of 2,3-diarylimidazo[1,2-a]pyridines.
引用
收藏
页码:5073 / 5078
页数:6
相关论文
共 50 条
  • [1] Copper-Catalyzed Aerobic Oxidative Cyclization of Ketoxime Acetates with Pyridines for the Synthesis of Imidazo[1,2-a]pyridines
    Ren, Zhi-Hui
    Zhao, Mi-Na
    Yi, Yukun
    Wang, Yao-Yu
    Guan, Zheng-Hui
    [J]. SYNTHESIS-STUTTGART, 2016, 48 (12): : 1920 - 1926
  • [2] Regioselective Oxidative Homocoupling Reaction: An Efficient Copper-Catalyzed Synthesis of Biimidazo[1,2-a]pyridines
    Lei, Sai
    Cao, Hua
    Chen, Longbin
    Liu, Jingyun
    Cai, Huiyin
    Tan, Jingwen
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (14-15) : 3109 - 3114
  • [3] Synthesis of Naphtho-Fused Imidazo[1,2-a]pyridines through Copper-Catalyzed Cascade Reactions
    Saini, Hitesh Kumar
    Kaswan, Pinku
    Pericherla, Kasiviswanadharaju
    Kumar, Anil
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 4 (12) : 1380 - 1385
  • [4] Copper-catalyzed C-N bond formation with imidazo[1,2-a]pyridines
    Sun, Kai
    Mu, Shiqiang
    Liu, Zhenhua
    Feng, Ranran
    Li, Yali
    Pang, Kui
    Zhang, Bing
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (36) : 6655 - 6658
  • [5] Copper-Catalyzed Intermolecular Oxidative Cyclization of Haloalkynes: Synthesis of 2-Halo-substituted Imidazo[1,2-a]pyridines, Imidazo[1,2-a]pyrazines and Imidazo[1,2-a]pyrimidines
    Gao, Yang
    Yin, Meizhou
    Wu, Wanqing
    Huang, Huawen
    Jiang, Huanfeng
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (11-12) : 2263 - 2273
  • [6] Copper-catalyzed three-component reaction to synthesize polysubstituted imidazo[1,2-a]pyridines
    Zhou, Zitong
    Luo, Danyang
    Li, Guanrong
    Yang, Zhongtao
    Cui, Liao
    Yang, Weiguang
    [J]. RSC ADVANCES, 2022, 12 (31) : 20199 - 20205
  • [7] 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
  • [8] Copper-Catalyzed Multicomponent Reactions (MCRs) for Disulfenylation of Imidazo[1,2-a]pyridines Using Elemental Sulfur and Arylhalides and Intramolecular Cyclization of Haloinnidazo[1,2-a]pyridines
    Semwal, Rashmi
    Ravi, Chitrakar
    Saxena, Soumya
    Adimurthy, Subbarayappa
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (21): : 14151 - 14160
  • [9] Copper-catalyzed intramolecular oxidative amination of enaminone C-H bond for the synthesis of imidazo[1,2-a]pyridines
    Wan, Jie-Ping
    Hu, Deqing
    Liu, Ying
    Li, Luyao
    Wen, Chengping
    [J]. TETRAHEDRON LETTERS, 2016, 57 (26) : 2880 - 2883
  • [10] Conversion of Pyridine to Imidazo[1,2-a]pyridines by Copper-Catalyzed Aerobic Dehydrogenative Cyclization with Oxime Esters
    Huang, Huawen
    Ji, Xiaochen
    Tang, Xiaodong
    Zhang, Min
    Li, Xianwei
    Jiang, Huanfeng
    [J]. ORGANIC LETTERS, 2013, 15 (24) : 6254 - 6257