Dienophilicity of imidazole in inverse electron demand Diels-Alder reactions; Intermolecular reactions with 1,2,4-triazines.

被引:16
|
作者
Wan, ZK [1 ]
Snyder, JK [1 ]
机构
[1] BOSTON UNIV,DEPT CHEM,BOSTON,MA 02215
基金
美国国家科学基金会;
关键词
D O I
10.1016/S0040-4039(97)01799-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Intermolecular cycloadditions between trialkyl 1,2,4-triazine-4,5,6-tricarboxylates and protected 2-aminoimidazole gave 1H-imidazo[4,5-c]pyridines (3-deazapurines) and the rearranged 3H-pyrido[3,2-d]pyrimid-4-ones (8-deazapteridines). No cycloadditions were observed with imidazole and 2-phenylimidazole. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:7495 / 7498
页数:4
相关论文
共 50 条
  • [21] Hydrazones as Productive Dienophiles in the Inverse Electron Demand Diels-Alder Reactions of 1,3,5-Triazines
    Yang, Kai
    Yang, Zhen
    Dang, Qun
    Bai, Xu
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (20) : 4344 - 4347
  • [22] DIELS-ALDER REACTIONS OF 1,2,4-TRIAZINES WITH CYCLIC VINYL ETHERS
    GONSALVES, AMDR
    MELO, TMVDPE
    GILCHRIST, TL
    TETRAHEDRON, 1993, 49 (24) : 5277 - 5290
  • [23] Carbohydrate auxiliaries in inverse electron demand Diels-Alder reactions.
    Nichols, SP
    DiCesare, JC
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U326 - U326
  • [24] Inverse-Electron-Demand Diels-Alder Reactions: Principles and Applications
    Png, Zhuang Mao
    Zeng, Huining
    Ye, Qun
    Xu, Jianwei
    CHEMISTRY-AN ASIAN JOURNAL, 2017, 12 (17) : 2142 - 2159
  • [25] SCOPE AND APPLICATION OF THE INVERSE ELECTRON DEMAND DIELS-ALDER REACTIONS OF AZADIENES
    BOGER, DL
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1990, 200 : 201 - ORGN
  • [26] Inverse electron demand Diels-Alder (IEDDA) reactions in peptide chemistry
    Pagel, Mareen
    JOURNAL OF PEPTIDE SCIENCE, 2019, 25 (01)
  • [27] Scope of the Inverse Electron Demand Diels-Alder Reactions of 1,2,3-Triazine
    Anderson, Erin D.
    Boger, Dale L.
    ORGANIC LETTERS, 2011, 13 (09) : 2492 - 2494
  • [28] Inverse electron demand Diels-Alder reactions using allenamides.
    Berry, CR
    Hsung, RP
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 226 : U195 - U195
  • [29] Inverse Electron Demand Diels-Alder Reactions of 1,2,3-Triazines: Pronounced Substituent Effects on Reactivity and Cycloaddition Scope
    Anderson, Erin D.
    Boger, Dale L.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (31) : 12285 - 12292
  • [30] INTRAMOLECULAR DIELS-ALDER REACTIONS OF 1,2,4-TRIAZINES - SYNTHESIS OF CONDENSED PYRIMIDINES
    TAYLOR, EC
    PONT, JL
    JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (19): : 4287 - 4292