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
  • [31] Aromatic Heterocycles as Productive Dienophiles in the Inverse Electron-Demand Diels-Alder Reactions of 1,3,5-Triazines
    Xu, Guoxing
    Bai, Xu
    Dang, Qun
    ACCOUNTS OF CHEMICAL RESEARCH, 2020, 53 (04) : 773 - 781
  • [32] Preparation of Carbohydrate Arrays by Using Diels-Alder Reactions with Inverse Electron Demand
    Beckmann, Henning S. G.
    Niederwieser, Andrea
    Wiessler, Manfred
    Wittmann, Valentin
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (21) : 6548 - 6554
  • [33] Inverse electron demand hetero Diels-Alder reactions of solid supported α-acilthiones
    Menichetti, S
    Mori, M
    Nativi, C
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2005, 180 (5-6) : 1327 - 1331
  • [34] Chelated Diborenes and Their Inverse-Electron-Demand Diels-Alder Reactions with Dienes
    Stennett, Tome.
    Mattock, James D.
    Pentecost, Leanne
    Vargas, Alfredo
    Braunschweig, Holger
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (46) : 15276 - 15281
  • [35] Inverse-Electron-Demand Diels-Alder Reactions for the Synthesis of Pyridazines on DNA
    Li, Hailong
    Sun, Zhen
    Wu, Wenting
    Wang, Xuan
    Zhang, Mingqiang
    Lu, Xiaojie
    Zhong, Wenge
    Dai, Dongcheng
    ORGANIC LETTERS, 2018, 20 (22) : 7186 - 7191
  • [37] Synthesis of Electron-Deficient 1,3,5-Triazines as Potential Azadienes for Inverse-Electron-Demand Diels-Alder Reactions
    Xu, Guoxing
    Zheng, Lianyou
    Wang, Shixue
    Dang, Qun
    Bai, Xu
    SYNTHETIC COMMUNICATIONS, 2010, 40 (03) : 361 - 369
  • [38] 2-Aminooxazoles as novel dienophiles in the inverse demand Diels-Alder reaction with 1,2,4-triazines
    Krinochkin, Alexey P.
    Reddy, Guda Mallikarjuna
    Kopchuk, Dmitry S.
    Slepukhin, Pavel A.
    Shtaitz, Yaroslav K.
    Khalymbadzha, Igor A.
    Kovalev, Igor S.
    Kim, Grigory A.
    Ganebnykh, Ilya N.
    Zyryanov, Grigory, V
    Chupakhin, Oleg N.
    Charushin, Valery N.
    MENDELEEV COMMUNICATIONS, 2021, 31 (04) : 542 - 544
  • [39] The inverse electron-demand' Diels-Alder reaction in polymer synthesis .3. Model Diels-Alder reactions of some bis(1,2,4-triazines with dienophiles and some bis-dienophiles with heterocyclic dienes
    McLean, GA
    Royles, BJL
    Smith, DM
    Bruce, MJ
    JOURNAL OF CHEMICAL RESEARCH-S, 1996, (10): : 448 - 449
  • [40] Transitions of electron demand in pericyclic reactions: Normal, neutral, and inverse Diels-Alder reactions of polyhalogenated cyclopentadienes
    Eibler, E
    Hocht, P
    Prantl, B
    Rossmaier, H
    Schuhbauer, HM
    Wiest, H
    Sauer, J
    LIEBIGS ANNALEN-RECUEIL, 1997, (12): : 2471 - 2484