Assembly of N-substituted pyrrolo[2,1-c][1,4]benzodiazepine-5,11-diones via copper catalyzed aryl amination

被引：16
作者：
Lu, Xu [1 ]
Shi, Liu [1 ]
Zhang, Hui [1 ]
Jiang, Yongwen [2 ]
Ma, Dawei [1 ]
机构：
[1] Shanghai Univ, Dept Chem, Shanghai 200444, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
来源：
TETRAHEDRON | 2010年 / 66卷 / 30期
基金：
中国国家自然科学基金;
关键词：
Aryl amination; Coupling; Benzodiazepine; Heterocycles; Amides; BOND FORMATION; CYCLIZATION; EFFICIENT; ARYLATION; HALIDES; ACCESS; AMINES;
D O I：
10.1016/j.tet.2010.04.127
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Copper-catalyzed amination of N-heterocycle derived aryl iodides followed by intramolecular condensative cyclization afforded N-substituted pyrrolo[2,1-c][1,4]-benzodiazepine-5,11-diones with good yields. By varying primary amines and substituents at aromatic ring of aryl iodides, a wide range of these heterocycles were assembled. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5714 / 5718
页数：5
相关论文
共 37 条
  • [1] Cu2O-catalyzed tandem ring-opening/coupling cyclization process for the synthesis of 2,3-dihydro-1,4-benzodioxins
    Bao, Weiliang
    Liu, Yunyun
    Lv, Xin
    Oian, Weixing
    [J]. ORGANIC LETTERS, 2008, 10 (17) : 3899 - 3902
  • [2] Synthesis and evaluation of acyl protein thioesterase 1 (APT1) inhibitors
    Biel, Markus
    Deck, Patrick
    Giannis, Athanassios
    Waldmann, Herbert
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (15) : 4121 - 4143
  • [3] Elaboration of 2-(trifluoromethyl)indoles via a cascade coupling/condensation/deacylation process
    Chen, Yu
    Wang, Yuji
    Sun, Zheming
    Ma, Dawei
    [J]. ORGANIC LETTERS, 2008, 10 (04) : 625 - 628
  • [4] Facile access to polysubstituted Indoles via a cascade Cu-catalyzed arylation - Condensation process
    Chen, Yu
    Xie, Xiaoan
    Ma, Dawei
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (24) : 9329 - 9334
  • [5] Synthesis of novel C2-aryl pyrrolobenzodiazepines (PBDs) as potential antitumour agents
    Cooper, N
    Hagan, DR
    Tiberghien, A
    Ademefun, T
    Matthews, CS
    Howard, PW
    Thurston, DE
    [J]. CHEMICAL COMMUNICATIONS, 2002, (16) : 1764 - 1765
  • [6] Copper-catalyzed cyclization of iodo-tryptophans:: A straightforward synthesis of pyrroloindoles
    Coste, Alexis
    Toumi, Mathieu
    Wright, Karen
    Razafimahaleo, Vanessa
    Couty, Francois
    Marrot, Jerome
    Evano, Gwilherm
    [J]. ORGANIC LETTERS, 2008, 10 (17) : 3841 - 3844
  • [7] Development and biological evaluation of acyl protein thioesterase 1 (APT1) inhibitors
    Deck, P
    Pendzialek, D
    Biel, M
    Wagner, M
    Popkirova, B
    Ludolph, B
    Kragol, G
    Kuhlmann, J
    Giannis, A
    Waldmann, H
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (31) : 4975 - 4980
  • [8] Assembly of Substituted 1H-Benzimidazoles and 1,3-Dihydrobenzimidazol-2-ones via CuI/L-Proline Catalyzed Coupling of Aqueous Ammonia with 2-Iodoacetanilides and 2-Iodophenylcarbamates
    Diao, Xiaoqiong
    Wang, Yuji
    Jiang, Yongwen
    Ma, Dawei
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (20) : 7974 - 7977
  • [9] Design, synthesis, and in vitro activity of peptidomimetic inhibitors of myeloid differentiation factor 88
    Fanto, Nicola
    Gallo, Grazia
    Ciacci, Andrea
    Semproni, Mauro
    Vignola, Davide
    Quaglia, Marco
    Bombardi, Valentina
    Mastroianni, Domenico
    Zibella, M. Pia
    Basile, Giancarlo
    Sassano, Marica
    Ruggiero, Vito
    De Santis, Rita
    Carminatit, Paolo
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (05) : 1189 - 1202
  • [10] FUNAMIZU H, 2005, Patent No. 6864250
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