Facile synthesis of 2-amino-3-bromoquinolines by palladium-catalyzed isocyanide insertion and cyclization of gem-dibromovinylanilines

被引：19
|
作者：
Jiang, Baishan [1 ]
Hu, Langxi [1 ]
Gui, Weijun [1 ]
机构：
[1] Chinese Acad Sci, Guangzhou Inst Biomed & Hlth, Inst Chem Biol, 190 Kaiyuan Ave, Guangzhou 510530, Guangdong, Peoples R China
来源：
RSC ADVANCES | 2014年 / 4卷 / 27期
关键词：
ONE-POT SYNTHESIS; REGIOSELECTIVE SYNTHESIS; DIHALOVINYL SYSTEMS; COUPLING REACTION; CROSS-COUPLINGS; TANDEM; DERIVATIVES; INDOLES; QUINOLINES; ANTAGONISTS;
D O I：
10.1039/c4ra00821a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A novel and efficient synthesis of 2-amino-3-bromoquinolines through palladium-catalyzed isocyanide insertion followed by intramolecular cyclization of gem-dibromovinylanilines was developed. The reactions were carried out in 1,4-dioxane at 100 degrees C for 2-3 h and the corresponding products were obtained in good isolated yields.
引用
收藏
页码：13850 / 13853
页数：4
相关论文
共 50 条
  • [1] Synthesis of 3-aryl-2-aminoquinolines: palladium-catalyzed cascade reactions of gem-dibromovinylanilines with tert-butyl isocyanide and arylboronic acids
    Hu, Langxi
    Gui, Weijun
    Liub, Zichen
    Jiang, Baishan
    RSC ADVANCES, 2014, 4 (72): : 38258 - 38262
  • [2] Synthesis of Pyridopyrimidines by Palladium-Catalyzed Isocyanide Insertion
    Estevez, Veronica
    Van Baelen, Gitte
    Lentferink, Babette H.
    Vlaar, Tjostil
    Janssen, Elwin
    Maes, Bert U. W.
    Orru, Romano V. A.
    Ruijter, Eelco
    ACS CATALYSIS, 2014, 4 (01): : 40 - 43
  • [3] Synthesis of 3-Iminoindol-2-amines and Cyclic Enaminones via Palladium-Catalyzed Isocyanide Insertion-Cyclization
    Pan, Yuan-Yuan
    Wu, Ya-Nan
    Chen, Zhen-Zhen
    Hao, Wen-Juan
    Li, Guigen
    Tu, Shu-Jiang
    Jiang, Bo
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (11): : 5764 - 5770
  • [4] Palladium-Catalyzed Domino Synthesis of 4-Amino-3-acyl-2-naphthols via Isocyanide Chemoselective Insertion
    Chen, Zhong
    Duan, Hua-Qing
    Jiang, Xiao
    Zhu, Yong-Ming
    Ji, Shun-Jun
    Yang, Shi-Lin
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (16): : 8183 - 8188
  • [5] Palladium-catalyzed synthesis of 5-amino-1,2,4-oxadiazoles via isocyanide insertion
    Wang, Xu
    Fu, Jin-Ping
    Xie, Jia-Xing
    Teng, Qing-Hu
    Tang, Hai-Tao
    Pan, Ying-Ming
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (26) : 4936 - 4940
  • [6] Synthesis of 3-Acyl-2-arylindole via Palladium-catalyzed Isocyanide Insertion and Oxypalladation of Alkyne
    Nanjo, Takeshi
    Yamamoto, Sho
    Tsukano, Chihiro
    Takemoto, Yoshiji
    ORGANIC LETTERS, 2013, 15 (14) : 3754 - 3757
  • [7] Palladium-Catalyzed Tandem Intramolecular Oxy/Amino-Palladation/Isocyanide Insertion: Synthesis of α-Benzofuranyl/Indolylacetamides
    Thirupathi, Nuligonda
    Babu, Madala Hari
    Dwivedi, Vikas
    Kant, Ruchir
    Reddy, Maddi Sridhar
    ORGANIC LETTERS, 2014, 16 (11) : 2908 - 2911
  • [8] Palladium-Catalyzed Synthesis of Amidines via tert-Butyl isocyanide Insertion
    Palinkas, Noemi
    Kollar, Laszlo
    Kegl, Tamas
    ACS OMEGA, 2018, 3 (11): : 16118 - 16126
  • [9] Palladium-catalyzed cyclization of o-alkynyltrifluoroacetanilides followed by isocyanide insertion: synthesis of 2-substituted 1H-indole-3-carboxamides
    Hu, Ziwei
    Liang, Dongdong
    Zhao, Jiaji
    Huang, Jinbo
    Zhu, Qiang
    CHEMICAL COMMUNICATIONS, 2012, 48 (59) : 7371 - 7373
  • [10] Carbonylative Synthesis of Thiochromenones via Palladium-Catalyzed tert -Butyl Isocyanide Insertion
    Zhang, Fang-Ling
    Chen, Zhen-Bang
    Liu, Kui
    Yuan, Qing
    Jiang, Qing
    Zhu, Yong-Ming
    SYNLETT, 2018, 29 (05) : 621 - 626
12345