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
  • [21] Silver-catalyzed [3+2]-cycloaddition of benzynes with diazocarbonyl species via a postulated (1H-indazol-1-yl)silver intermediate
    Wang, Chiou-Dong
    Liu, Rai-Shung
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (45) : 8948 - 8952
  • [22] Silver-Catalyzed Isocyanide-Isocyanide [3+2] Cross-Cycloaddition Involving 1,2-Group Migration: Efficient Synthesis of Trisubstituted lmidazoles
    Wang, Hongwei
    Kumar, Rapolu Kiran
    Yu, Yang
    Zhang, Lin
    Liu, Zhaohong
    Liao, Peiqiu
    Bi, Xihe
    CHEMISTRY-AN ASIAN JOURNAL, 2016, 11 (20) : 2841 - 2845
  • [23] Silver-catalyzed formal [3+2]-cycloaddition of α-trifluoromethylated methyl isocyanides: a facile stereoselective synthesis of CF3-substituted heterocycles
    Zhang, Xue
    Wang, Xin
    Gao, Yuelei
    Xu, Xianxiu
    CHEMICAL COMMUNICATIONS, 2017, 53 (16) : 2427 - 2430
  • [24] A silver-catalyzed stereoselective domino cycloisomerization-vinylogous aldol reaction of ortho-alkynylbenzaldehydes with 3-alkylidene oxindoles: an entry to functionalized isochromenes
    Kumar, Krishna
    Singh, Bhuvnesh
    Singh, Ravi P.
    CHEMICAL COMMUNICATIONS, 2020, 56 (96) : 15153 - 15156
  • [25] Synthesis of 1-Phospho-3-benzoxepins via a Silver-catalyzed Reaction of 2-Alkynylacetophenones with Diazomethylphosphonates
    She, Rui
    Qiu, Jialin
    Liu, Yan
    Peng, Yungui
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (10) : 1580 - 1584
  • [26] Silver-Catalyzed exo-dig-Azacyclization/[3+2] Cycloaddition Cascades on 1-Tosylhydrazon-4-oxy-5-yne Substrates: Applicability to Diverse Alkenes
    Huple, Deepak B.
    Chen, Chun-Hao
    Das, Arindam
    Liu, Rai-Shung
    ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (11-12) : 1877 - 1882
  • [27] Silver-catalyzed regioselective [3+2] cycloaddition of arene-diazonium salts with 2,2,2-trifluorodiazoethane (CF3CHN2): a facile access to 2-aryl-5-trifluoromethyltetrazoles
    Chen, Zhen
    Fan, Shuang-Qing
    Zheng, Yan
    Ma, Jun-An
    CHEMICAL COMMUNICATIONS, 2015, 51 (92) : 16545 - 16548
  • [28] Silver-catalyzed [3+2] cycloaddition of isocyanides with diazo compounds: new regioselective access to 1,4-disubstituted-1,2,3-triazoles
    Wang, Shuai
    Yang, Li-Jun
    Zeng, Jun-Liang
    Zheng, Yan
    Ma, Jun-An
    ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (11): : 1468 - 1474
  • [29] An Efficient Domino Approach for the Synthesis of Multisubstituted Pyrroles via Gold/Silver-Catalyzed Amination/Cycloisomerization of (Z)-2-En-4-yn-1-ols
    Lu, Yuhua
    Fu, Xiaoping
    Chen, Haoyi
    Du, Xiangwei
    Jia, Xueshun
    Liu, Yuanhong
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (1-2) : 129 - 134
  • [30] Thiourea-Catalyzed Domino Michael-Mannich [3+2] Cycloadditions: A Strategy for the Asymmetric Synthesis of 3,3-Pyrrolidinyl-dispirooxindoles
    Zhi, Ying
    Zhao, Kun
    von Essen, Carolina
    Rissanen, Kari
    Enders, Dieter
    SYNLETT, 2017, 28 (20) : 2876 - 2880