Palladium-Catalyzed Tandem Regioselective Oxidative Coupling from Indoles and Maleimides: One-Pot Synthesis of Indolopyrrolocarbazoles and Related Indolylmaleimides

被引：57
|
作者：
An, Yu-Long [1 ]
Yang, Zhen-Hua [1 ]
Zhang, He-Hui [1 ]
Zhao, Sheng-Yin [1 ,2 ]
机构：
[1] Donghua Univ, Dept Chem, Shanghai 201620, 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：
ORGANIC LETTERS | 2016年 / 18卷 / 02期
关键词：
C-H FUNCTIONALIZATION; BIOLOGICAL EVALUATION; MICHAEL ADDITION; INDOLOCARBAZOLE; ALKENYLATION; PYRROLES; ANALOGS; SYSTEM; DERIVATIVES; CARBAZOLES;
D O I：
10.1021/acs.orglett.5b02944
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient Pd(II)-catalyzed approach for the direct synthesis of indolo[3,2-a]pyrrolo[3,4-c]carbazole-6,8-diones has been developed from both free and protected (NH) indoles and maleimides via a regioselective tandem oxidative coupling reaction. The yields are moderate to excellent. In addition, 2-substituted indoles are suitable substrates in this protocol, leading to the formation of indolylmaleimides. The present methodology provides a concise route to highly functionalized indolopyrrolocarbazole derivatives.
引用
收藏
页码：152 / 155
页数：4
相关论文
共 50 条
  • [1] Palladium-Catalyzed Regioselective Oxidative Coupling of Indoles and One-Pot Synthesis of Acetoxylated Biindolyls
    Liang, Zuijun
    Zhao, Jinlong
    Zhang, Yuhong
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (01): : 170 - 177
  • [2] A palladium-catalyzed one-pot procedure for the regioselective dimerization and cyanation of indoles
    Kianmehr, Ebrahim
    Ghanbari, Mohammad
    Faghih, Nasser
    Rominger, Frank
    [J]. TETRAHEDRON LETTERS, 2012, 53 (15) : 1900 - 1904
  • [3] Tandem one-pot palladium-catalyzed reductive and oxidative coupling of benzene and chlorobenzene
    Mukhopadhyay, S
    Rothenberg, G
    Gitis, D
    Sasson, Y
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10): : 3107 - 3110
  • [4] One-pot synthesis of carbazoles by palladium-catalyzed N-arylation and oxidative coupling
    Watanabe, Toshiaki
    Ueda, Satoshi
    Inuki, Shinsuke
    Oishi, Shinya
    Fujii, Nobutaka
    Ohno, Hiroaki
    [J]. CHEMICAL COMMUNICATIONS, 2007, (43) : 4516 - 4518
  • [5] One-pot synthesis of carbazoles by palladium-catalyzed N-arylation and oxidative coupling
    Watanabe, Toshiaki
    Inuki, Shinsuke
    Ueda, Satoshi
    Oishi, Shinya
    Ohno, Hiroaki
    Fujii, Nobutaka
    [J]. DRUGS OF THE FUTURE, 2007, 32 : 136 - 137
  • [6] ONE-POT PALLADIUM-CATALYZED SYNTHESIS OF DIARYLALKYNES
    CARPITA, A
    LESSI, A
    ROSSI, R
    [J]. SYNTHESIS-STUTTGART, 1984, (07): : 571 - 572
  • [7] An Approach to One-Pot Regioselective Synthesis of Indenones through Palladium-Catalyzed Annulation in Water
    Ramesh, Karu
    Satyanarayana, Gedu
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (30) : 4135 - 4146
  • [8] Palladium-Catalyzed Acylations: One-Pot Synthesis of Indenones
    Suchand, Basuli
    Satyanarayana, Gedu
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (01): : 372 - 381
  • [9] Palladium-catalyzed tandem one-pot synthesis of π-expanded imidazoles through a sequential Heck and oxidative amination reaction
    Li, Xue
    Chen, Xin
    Wang, Hui
    Chen, Chunxia
    Sun, Peng
    Mo, Baichuan
    Peng, Jinsong
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (16) : 4014 - 4023
  • [10] Pd(II) supramolecular cage-catalyzed successive oxidative coupling: One-pot and regioselective synthesis of functionalized carbazoles from indoles
    Wu, Xi-Ren
    Peng, He-Long
    Wei, Lian-Qiang
    Li, Li-Ping
    Yao, Su-Yang
    Ye, Bao-Hui
    [J]. CATALYSIS COMMUNICATIONS, 2019, 124 : 12 - 18
12345