Bronsted acid-catalyzed synthesis of carbazoles from 2-substituted indoles

被引：8
|
作者：
Li, Qingjiang [1 ,2 ]
Peng, Xiao-Shui [1 ,2 ,3 ,4 ]
Wong, Henry N. C. [1 ,2 ,3 ,4 ]
机构：
[1] Chinese Univ Hong Kong, Ctr Novel Funct Mol, Dept Chem, Shatin, Hong Kong, Peoples R China
[2] Chinese Univ Hong Kong, State Key Lab Synthet Chem, Shatin, Hong Kong, Peoples R China
[3] Chinese Univ Hong Kong, Shenzhen Municipal Key Lab Chem Synth Med Organ M, Shenzhen 518507, Peoples R China
[4] Chinese Univ Hong Kong, Shenzhen Ctr Novel Funct Mol, Shenzhen Res Inst, Shenzhen 518507, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2014年 / 1卷 / 10期
基金：
中国国家自然科学基金;
关键词：
1ST TOTAL-SYNTHESIS; DOUBLE N-ARYLATION; TRANSITION-METAL-COMPLEXES; ORGANIC-SYNTHESIS; CLAUSINE-L; BISCARBAZOLE ALKALOIDS; CONSECUTIVE AMINATION; MEDIATED SYNTHESIS; PRIMARY AMINES; BOND FORMATION;
D O I：
10.1039/c4qo00242c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple and efficient method for the synthesis of disubstituted carbazoles has been developed. In this approach, carbazoles are synthesized from o-haloanilines and terminal alkynes using a two-step strategy, namely, Sonogashira coupling and intramolecular cyclization to provide indoles, which are followed by a p-TSA center dot H2O-catalyzed carbazole formation.
引用
收藏
页码：1197 / 1200
页数：4
相关论文
共 50 条
  • [1] Bronsted Acid-Catalyzed Straightforward Synthesis of Benzo[b]carbazoles from 2,3-Unsubstituted Indoles
    Suarez, Anisley
    Garcia-Garcia, Patricia
    Fernandez-Rodriguez, Manuel A.
    Sanz, Roberto
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (2-3) : 374 - 382
  • [2] PALLADIUM CATALYZED SYNTHESIS OF 2-SUBSTITUTED INDOLES
    RUDISILL, DE
    STILLE, JK
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1988, 196 : 37 - ORGN
  • [3] Synthesis of Fused Polycyclic Indoles by Bronsted Acid-Catalyzed Intramolecular Alkylation of Indoles with Alcohols
    Suarez, Anisley
    Gohain, Mukut
    Fernandez-Rodriguez, Manuel A.
    Sanz, Roberto
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (20): : 10421 - 10430
  • [4] From Indoles to Carbazoles: Tandem Cp*Rh(III)-Catalyzed C-H Activation/Bronsted Acid-Catalyzed Cyclization Reactions
    Wu, Jia-Qiang
    Yang, Zhen
    Zhang, Shang-Shi
    Jiang, Chun-Yong
    Li, Qingjiang
    Huang, Zhi-Shu
    Wang, Honggen
    ACS CATALYSIS, 2015, 5 (11): : 6453 - 6457
  • [5] Bronsted Acid-Catalyzed the Synthesis of Sulfoximide Substituted Dihydropyranone Derivatives
    Sun Xinhao
    Duan Xuelun
    Song Wangze
    Jiang Wenfeng
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (02) : 487 - 497
  • [6] PALLADIUM-CATALYZED SYNTHESIS OF 2-SUBSTITUTED INDOLES
    RUDISILL, DE
    STILLE, JK
    JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (25): : 5856 - 5866
  • [7] SYNTHESIS OF 2-SUBSTITUTED INDOLES
    ZAVYALOV, SI
    ZAVOZIN, AG
    DOROFEEVA, OV
    RUMYANTSEVA, EE
    BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1991, 40 (02): : 441 - 443
  • [8] Chiral Bronsted acid-catalyzed enantioselective addition of indoles to ketimines
    Kano, Taichi
    Takechi, Ryosuke
    Kobayashi, Ryohei
    Maruoka, Keiji
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (05) : 724 - 727
  • [9] Synthesis of N-vinyl substituted indoles and their acid-catalyzed behavior
    Li, Hao
    Boonnak, Nawong
    Padwa, Albert
    TETRAHEDRON LETTERS, 2011, 52 (17) : 2062 - 2064
  • [10] Facile Synthesis of Trisubstituted Carbazoles by Acid-Catalyzed Ring-Opening Annulation of 2-Amidodihydrofurans with Indoles
    Zhao, Jingjing
    Li, Pan
    Xia, Chungu
    Li, Fuwei
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (46) : 16383 - 16386
12345