One-pot synthesis of 1,2,4,5-tetrasubstituted imidazoles by a tandem three-component reaction of hydroxylamines, aldehydes and 2-azido acrylates

被引：9
作者：
Hu, Bao [1 ,2 ]
Ai, Ning [1 ]
Wang, Zhao [1 ]
Xu, Xiaoliang [1 ,2 ]
Li, Xiaonian [1 ,2 ]
机构：
[1] Zhejiang Univ Technol, Coll Chem Engn & Mat Sci, Hangzhou 310014, Zhejiang, Peoples R China
[2] Zhejiang Univ Technol, Inst Ind Catalysis, Hangzhou 310014, Zhejiang, Peoples R China
来源：
ARKIVOC | 2012年
关键词：
Hydroxylamines; aldehydes; 2-azido acrylates; multicomponent reactions; imidazoles; ANTITUMOR-ACTIVITY; VINYL AZIDES; PYRROLES; 2-AZIDOACRYLATES; ISOQUINOLINES; PYRIDINES; INDOLES; OXAZOLE; ANALOGS; AGENTS;
D O I：
10.3998/ark.5550190.0013.621
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reaction of nitrones, formed in situ by reaction of hydroxylamines and aldehydes, with 2-azido acrylates results in the formation of 1,2,4,5-tetrasubstituted imidazoles has been developed. This three-component reaction allows for the formation of a diverse array of imidazole derivatives with moderate to excellent yields.
引用
收藏
页码：222 / 228
页数：7
相关论文
共 29 条
  • [1] Analogues of 4,5-bis(3,5-dichlorophenyl)-2-trifluoromethyl-1H-imidazole as potential antibacterial agents.
    Antolini, M
    Bozzoli, A
    Ghiron, C
    Kennedy, G
    Rossi, T
    Ursini, A
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (07) : 1023 - 1028
  • [2] DNA-directed alkylating agents. 7. Synthesis, DNA interaction, and antitumor activity of bis(hydroxymethyl)- and bis(carbamate)-substituted pyrrolizines and imidazoles
    Atwell, GJ
    Fan, JY
    Tan, K
    Denny, WA
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (24) : 4744 - 4754
  • [3] Beckmann E., 1909, LIEBIGS ANN CHEM, V365, P201
  • [4] SULPHUR-METHYLENE ISOSTERISM IN DEVELOPMENT OF METIAMIDE, A NEW HISTAMINE H2-RECEPTOR ANTAGONIST
    BLACK, JW
    DURANT, GJ
    EMMETT, JC
    GANELLIN, CR
    [J]. NATURE, 1974, 248 (5443) : 65 - 67
  • [5] Iron(II) Triflate as a Catalyst for the Synthesis of Indoles by Intramolecular C-H Amination
    Bonnamour, Julien
    Bolm, Carsten
    [J]. ORGANIC LETTERS, 2011, 13 (08) : 2012 - 2014
  • [6] Domino Approach for the Synthesis of Pyrrolo[1,2-a]pyrazine from Vinyl Azides
    Chen, Wenteng
    Hu, Miao
    Wu, Jianwei
    Zou, Hongbin
    Yu, Yongping
    [J]. ORGANIC LETTERS, 2010, 12 (17) : 3863 - 3865
  • [7] A Cascade Approach to Pyridines from 2-Azido-2,4-dienoates and α-Diazocarbonyl Compounds
    Chen, Zheng-Bo
    Hong, Deng
    Wang, Yan-Guang
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (02) : 903 - 905
  • [8] Synthesis of polysubstituted N-H pyrroles from vinyl azides and 1,3-dicarbonyl compounds
    Chiba, Shunsuke
    Wang, Yi-Feng
    Lapointe, Guillaume
    Narasaka, Koichi
    [J]. ORGANIC LETTERS, 2008, 10 (02) : 313 - 316
  • [9] N-alkoxyacrylamides as substrates for enantioselective Diels-Alder reactions
    Corminboeuf, O
    Renaud, P
    [J]. ORGANIC LETTERS, 2002, 4 (10) : 1735 - 1738
  • [10] Antifungal agents.: 11.: N-substituted derivatives of 1-[(aryl)(4-aryl-1H-pyrrol-3-yl)methyl]-1H-imidazole:: Synthesis, anti-Candida activity, and QSAR studies
    Di Santo, R
    Tafi, A
    Costi, R
    Botta, M
    Artico, M
    Corelli, F
    Forte, M
    Caporuscio, F
    Angiolella, L
    Palamara, AT
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (16) : 5140 - 5153
123