Silver-catalyzed [3+2] domino reaction: an efficient strategy to synthesize imidazole-5-carbaldehydes

被引:11
|
作者
Wang, Changcheng [1 ,2 ]
Jiang, Hangqi [1 ,2 ]
Chen, Weifeng [1 ,2 ]
Dong, Jun [3 ]
Chen, Zhengwang [4 ]
Cao, Hua [1 ,2 ]
机构
[1] Guangdong Pharmaceut Univ, Sch Chem & Chem Engn, Zhongshan 528458, Peoples R China
[2] Guangdong Pharmaceut Univ, Guangdong Cosmet Engn & Technol Res Ctr, Zhongshan 528458, Peoples R China
[3] Guangdong Pharmaceut Univ, Sch Tradit Chinese Med, Guangzhou 510006, Guangdong, Peoples R China
[4] Gannan Normal Univ, Key Lab Organopharmaceut Chem Jiangxi Prov, Ganzhou 341000, Peoples R China
基金
中国国家自然科学基金;
关键词
C-H BONDS; HIGHLY SUBSTITUTED IMIDAZOLES; ONE-POT; REGIOSELECTIVE SYNTHESIS; MOLECULAR-OXYGEN; TETRASUBSTITUTED IMIDAZOLES; DIRECT ARYLATION; METAL-FREE; MULTICOMPONENT SYNTHESIS; 3-COMPONENT REACTION;
D O I
10.1039/c7ob01242j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An unprecedented regioselective silver-catalyzed [3 + 2] domino reaction of amidines and ynals for the formation of C-N bonds has been developed. The reaction provided a new route to prepare imidazole-5-carbaldehydes which are important intermediates for the construction of fine chemicals. The reaction proceeds smoothly with a broad range of substrates to give imidazoles in good yields.
引用
收藏
页码:6463 / 6466
页数:4
相关论文
共 50 条
  • [41] Silver-Catalyzed 5-Exo-dig Cyclization Reaction of ortho-Hydroxyphenylpropargyl Alcohols to 2-Methylene-2,3-dihydrobenzofuran
    Feng Miao
    Lu Lanlan
    Guo Yijia
    Liu Jianquan
    Wang Xianshan
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (04) : 1218 - 1225
  • [42] A silver-catalyzed domino inverse electron-demand oxo-Diels-Alder reaction of 3-cyclopropylideneprop-2-en-1-ones with 2,3-dioxopyrrolidines via cyclobutane-fused furan
    Zhang, Yanshun
    Wei, Yin
    Shi, Min
    CHEMICAL COMMUNICATIONS, 2021, 57 (29) : 3599 - 3602
  • [43] Silver(I)-Catalyzed Enantioselective [3+2]-Cycloaddition Reaction of α-Silylimines: A Facile Route to Quaternary-Carbon-Rich Scaffolds
    Kesava-Reddy, Naredla
    Golz, Christopher
    Strohmann, Carsten
    Kumar, Kamal
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (51) : 18373 - 18377
  • [44] Highly efficient synthesis of 2,3,4-trisubstituted furans via silver-catalyzed sequential nucleophilic addition and cyclization reactions of haloalkynes
    Zeng, Wei
    Wu, Wanqing
    Jiang, Huanfeng
    Sun, Yadong
    Chen, Zhengwang
    TETRAHEDRON LETTERS, 2013, 54 (35) : 4605 - 4609
  • [45] Silver-catalyzed radical reaction of 2H-indazoles with 1,3-dicarbonyl compounds to access 3-dicarbonyl indazoles
    Li, Zhen-Hua
    Wang, Wen-Biao
    Qin, Jin-Jing
    Ye, Li-Xian
    He, Jia-Yu
    Xie, Yuan-Yuan
    TETRAHEDRON, 2021, 91
  • [46] Amine-Catalyzed [3+2] Huisgen Cycloaddition Strategy for the Efficient Assembly of Highly Substituted 1,2,3-Triazoles
    Wang, Lei
    Peng, Shiyong
    Danence, Lee Jin Tu
    Gao, Yaojun
    Wang, Jian
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (19) : 6088 - 6093
  • [47] Simultaneous Construction of C-N Axial and Central Chirality via Silver-Catalyzed Desymmetrizative [3+2] Cycloaddition of Prochiral N-Aryl Maleimides with Activated Isocyanides
    Zhang, Sen
    Luo, Zhang-Hong
    Wang, Wen-Tao
    Qian, Linghui
    Liao, Jia-Yu
    ORGANIC LETTERS, 2022, 24 (25) : 4645 - 4649
  • [48] Silver-catalyzed cascade cyclization-stannylation of o-alkynylaniline derivatives with 2-tributylstannylfuran: an efficient synthesis of (3-indolyl) stannanes
    Liu, Jun
    Xie, Xin
    Liu, Yuanhong
    CHEMICAL COMMUNICATIONS, 2013, 49 (100) : 11794 - 11796
  • [49] Silver-Catalyzed Tandem Cycloisomerization/[5+2] Cycloaddition of 3-Cyclopropylideneprop-2-en-1-ones with Oxidopyrylium Ylides to Form Bibridged Benzocycloheptanones
    Huang, Jing
    Liang, Yushuang
    Sun, Shengnan
    Zhang, Ruilong
    Miao, Zhiwei
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (13): : 8454 - 8464
  • [50] Aniline Dearomatization and Silver-Catalyzed [3+3] Dipolar Cycloaddition: Efficient Construction of Oxocino[4,3,2-cd]indoles from 2-Alkynylanilines and 2-Alkynylbenzaldoximes
    Han, Dandan
    He, Qiuqin
    Fan, Renhua
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (47) : 14013 - 14016