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
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 50 条
  • [1] Microwave assisted synthesis of pyrrolo[2,1-c][1,4]benzodiazepine-5,11-diones
    Kamal, A
    Reddy, BSN
    Reddy, GSK
    SYNLETT, 1999, (08) : 1251 - 1252
  • [2] THE NONCOVALENT INTERACTION OF PYRROLO[2,1-C] [1,4]BENZODIAZEPINE-5,11-DIONES WITH DNA
    JONES, GB
    DAVEY, CL
    JENKINS, TC
    KAMAL, A
    KNEALE, GG
    NEIDLE, S
    WEBSTER, GD
    THURSTON, DE
    ANTI-CANCER DRUG DESIGN, 1990, 5 (03): : 249 - 264
  • [3] Solid-phase synthesis of pyrrolo[2,1-c][1,4]benzodiazepine-5,11-diones
    Kamal, A
    Reddy, GSK
    Raghavan, S
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (03) : 387 - 389
  • [4] An expedient synthesis of 7-O-functionalised pyrrolo[2,1-c][1,4]benzodiazepine-5,11-diones
    Madani, H
    Thompson, AS
    Threadgill, MD
    TETRAHEDRON, 2002, 58 (40) : 8107 - 8111
  • [5] Syntheses of N10-substituted 7-Arylpyrrolo[2,1-c]-[1,4]benzodiazepine-5,11-diones
    Lindner, Anika Sabine
    Geist, Egor
    Gjikaj, Mimoza
    Schmidt, Andreas
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2014, 51 (02) : 423 - 431
  • [6] Pyrrolo[2,1-c][1,4]benzodiazepine-5,11-dithione
    Ourahou, Sarah
    Zouihri, Hafid
    Essassi, El Mokhtar
    Ng, Seik Weng
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O1653 - U128
  • [7] Solid-phase synthesis of a library of pyrrolo[2,1-c][1,4]benzodiazepine-5,11-diones with potential antitubercular activity
    Kamal, Ahmed
    Reddy, K. Laxma
    Devaiah, V.
    Shankaraiah, N.
    Reddy, G. Suresh Kumar
    Raghavan, Sadagopan
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2007, 9 (01): : 29 - 42
  • [8] Hydride reductions of 1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11-diones:: Selective reduction of secondary amides to carbinolamines
    Katsifis, AG
    McPhee, ME
    Ridley, DD
    AUSTRALIAN JOURNAL OF CHEMISTRY, 1998, 51 (12) : 1121 - 1130
  • [9] Glycosyl-pyrrolo [2,1-c][1,4]benzodiazepine-5,11-diones.: Synthesis, tensioactivity and antibacterial activity
    Bouhlal, D
    Godé, P
    Goethals, G
    Massoui, M
    Villa, P
    Martin, P
    HETEROCYCLES, 2001, 55 (02) : 303 - 312
  • [10] Efficient reduction of aromatic nitro/azido groups on solid support employing indium:: synthesis of pyrrolo[2,1-c][1,4]benzodiazepine-5,11-diones
    Kamal, A
    Reddy, GSK
    Reddy, KL
    TETRAHEDRON LETTERS, 2001, 42 (39) : 6969 - 6971