The first iodine improved 1,3-dipolar cycloaddition: facile and novel synthesis of 2-substituted benzo[f]isoindole-4,9-diones

被引：17
作者：
Huang, Huan-Ming [1 ]
Gao, Jian-Rong [1 ]
Hou, Li-Fen [2 ]
Jia, Jian-Hong [1 ]
Han, Liang [1 ]
Ye, Qing [1 ]
Li, Yu-Jin [1 ]
机构：
[1] Zhejiang Univ Technol, State Key Lab Breeding Base Green Chem Synth Tech, Hangzhou 310032, Zhejiang, Peoples R China
[2] Zhengzhou Univ, Coll Chem & Mol Engn, Zhengzhou 450001, Peoples R China
来源：
TETRAHEDRON | 2013年 / 69卷 / 43期
关键词：
2-Substituted benzo[f]isoindole-4,9-dione; 1,3-Dipolar cycloaddition; Quinones; N-Substituted amino ester hydrochlorides; Iodine; MOLECULAR-IODINE; AZOMETHINE YLIDES; OXIDATIVE CONVERSION; EFFICIENT SYNTHESIS; DERIVATIVES; 2H-ISOINDOLE-4,7-DIONES; QUINONES; ALCOHOLS; INDOLES; IMINES;
D O I：
10.1016/j.tet.2013.08.029
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first novel protocol of the synthesis of 2-substituted benzo[f]indole-4,9-dione framework via the one-pot, 1,3-dipolar cycloaddition of quinones, paraformaldehyde and N-substituted amino ester hydrochlorides in the present of iodine at refluxing acetonitrile was reported. All these reactions proceed with good to excellent yields. The promising results obtained 1,3-dipolar cycloaddition will have the potential application in natural product exhibiting important biological activities. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：9033 / 9037
页数：5
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共 58 条
  • [1] Novel dipolarophiles and dipoles in the metal-catalyzed enantioselective 1,3-dipolar cycloaddition of azomethine ylides
    Adrio, Javier
    Carretero, Juan C.
    [J]. CHEMICAL COMMUNICATIONS, 2011, 47 (24) : 6784 - 6794
  • [2] INDOLE BETA-NUCLEOPHILIC SUBSTITUTION .5. SYNTHESIS OF THE 4 ISOMERIC 5H-PYRIDO[X,Y-B]CARBAZOLE-5,11-DIONES AND BENZO ANALOGS
    ASHCROFT, WR
    DALTON, L
    BEAL, MG
    HUMPHREY, GL
    JOULE, JA
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (10): : 2409 - 2412
  • [3] Molecular iodine-catalyzed efficient and highly rapid synthesis of bis(indolyl)methanes under mild conditions
    Bandgar, BP
    Shaikh, KA
    [J]. TETRAHEDRON LETTERS, 2003, 44 (09) : 1959 - 1961
  • [4] Iodine-catalyzed highly efficient Michael reaction of indoles under solvent-free condition
    Banik, BK
    Fernandez, M
    Alvarez, C
    [J]. TETRAHEDRON LETTERS, 2005, 46 (14) : 2479 - 2482
  • [5] Synthesis of novel spirooxindole derivatives by one pot multicomponent reaction and their antimicrobial activity
    Bhaskar, Gangaru
    Arun, Yuvaraj
    Balachandran, Chandrasekar
    Saikumar, Chandrasekara
    Perumal, Paramasivan T.
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 51 : 79 - 91
  • [6] ACTIVITY OF GR30921X (NSC-382057) AND GR63178A (NSC-D611615) IN HUMAN OVARIAN-CANCER LINES
    BOVEN, E
    ERKELENS, CAM
    LUNING, M
    PINEDO, HM
    [J]. BRITISH JOURNAL OF CANCER, 1990, 61 (05) : 709 - 711
  • [7] Creative approaches towards the synthesis of 2,5-dihydro- furans, thiophenes, and pyrroles. One method does not at all!
    Brichacek, Matthew
    Njardarson, Jon T.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (09) : 1761 - 1770
  • [8] Synthesis of benzo[f]isoindole-4,9-diones
    Claessens, Sven
    Jacobs, Jan
    Van Aeken, Sam
    Tehrani, Kourosch Abbaspour
    De Kimpe, Norbert
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (19) : 7555 - 7559
  • [9] Intramolecular dipolar cycloaddition reactions of azomethine ylides
    Coldham, I
    Hufton, R
    [J]. CHEMICAL REVIEWS, 2005, 105 (07) : 2765 - 2809
  • [10] A New Synthesis of Benzo[f]isoindole-4,9-diones by Radical Alkylation and Bromomethylation of 1,4-Naphthoquinones
    Deblander, Jurgen
    Van Aeken, Sam
    Jacobs, Jan
    De Kimpe, Norbert
    Tehrani, Kourosch Abbaspour
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (28) : 4882 - 4892
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