An Efficient Route to 3-Amidylindoles via a Palladium- Catalyzed Tandem Reaction of 2-Alkynylanilines with Isocyanides

被引：53
|
作者：
Qiu, Guanyinsheng [1 ]
Chen, Chen [2 ]
Yao, Liangqing [2 ]
Wu, Jie [1 ,3 ]
机构：
[1] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China
[2] Fudan Univ, Obstet & Gynecol Hosp, 419 Fangxie Rd, Shanghai 200011, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2013年 / 355卷 / 08期
基金：
中国国家自然科学基金;
关键词：
3-amidylindoles; N; N-dimethyl-2-alkynylanilines; isocyanides; palladium catalyst; tandem reactions; FUNCTIONALIZED INDOLES; 3-COMPONENT REACTION; CASCADE REACTIONS; ARYL HALIDES; INSERTION; ALKYNES; HETEROCYCLES; CONSTRUCTION; CYCLIZATION; ACTIVATION;
D O I：
10.1002/adsc.201300198
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A palladium-catalyzed reaction of 2-alkynylaniline, isocyanides, and silver acetate is described, leading to 3-amidylindoles in moderate to good yields. During the process, five new bonds are formed with high reaction efficiency in one-pot procedure.
引用
收藏
页码：1579 / 1584
页数：6
相关论文
共 50 条
  • [21] Aniline Dearomatization and Silver-Catalyzed [3+3] Dipolar Cycloaddition: Efficient Construction of Oxocino[4,3,2-cd]indoles from 2-Alkynylanilines and 2-Alkynylbenzaldoximes
    Han, Dandan
    He, Qiuqin
    Fan, Renhua
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (47) : 14013 - 14016
  • [22] A New Efficient Synthetic Route for the Synthesis of the Antiallergic Drug, Olopatadine Hydrochloride, via Stereospecific Palladium-Catalyzed Reaction
    Nishimura, Koichiro
    Kinugawa, Masahiko
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2012, 16 (02) : 225 - 231
  • [23] Gold(I)-catalyzed one-pot reaction between 2-alkynylanilines and alkynols leading to the formation of C-3-substituted indoles: a case of formal carboamination of alkynes
    Patil, Nitin T.
    Singh, Vipender
    Konala, Ashok
    Mutyala, Anil Kumar
    TETRAHEDRON LETTERS, 2010, 51 (11) : 1493 - 1496
  • [24] Generation of 4-Cyanoisoquinolines and 4-Amidylisoquinolines via a Palladium-Catalyzed Cyanative Reaction of 2-Alkynylbenzaldimines with Isocyanides
    Qiu, Guanyinsheng
    Qiu, Xiaochen
    Wu, Jie
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (16) : 3205 - 3209
  • [25] Stereoselective Synthesis of 3-(1,3-Diarylallylidene)oxindoles via a Palladium-Catalyzed Tandem Reaction
    Yu, Yoseb
    Shin, Kye Jung
    Seo, Jae Hong
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (03): : 1864 - 1871
  • [26] Perfluorous superacid C8F17SO3H-catalyzed intramolecular hydroamination reaction of N-protected 2-alkynylanilines:: a novel synthetic method for indoles
    Yin, Yan
    Zhao, Gang
    CHIMICA OGGI-CHEMISTRY TODAY, 2007, 25 (03) : 42 - 45
  • [27] Accessing indole-isoindole derivatives via palladium-catalyzed [3+2] cyclization of isocyanides with alkynyl imines
    Chen, Dianpeng
    Li, Jianming
    Liu, Gongle
    Zhang, Xiuhua
    Wang, Xin
    Liu, Yongwei
    Liu, Xuan
    Liu, Xinghai
    Li, Yongqin
    Shan, Yingying
    CHEMICAL COMMUNICATIONS, 2023, 59 (70) : 10540 - 10543
  • [28] Enantioselective Synthesis of Indole-Derivated Axially Chiral Frameworks via CpXRh(III)-Catalyzed Domino Cyclization/C3-Arylation of 2-Alkynylanilines with 1-Diazonaphthoquinones
    Ye, Junwei
    Song, Qingwei
    Pan, Dongping
    Zeng, Zhongyi
    Gao, Hui
    Xu, Huiying
    Yi, Wei
    Zhou, Zhi
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (05) : 1064 - 1069
  • [29] Additive-Controlled Divergent Synthesis of Indole and 4H-Benzo[d][1,3]oxazine Derivatives: Palladium-Catalyzed Carbonylative Cyclization of 2-Alkynylanilines and Benzyl Chlorides
    Wang, Qi
    Yao, Lingyun
    Wang, Jian-Shu
    Ying, Jun
    Wu, Xiao-Feng
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (05): : 3874 - 3882
  • [30] Palladium-Catalyzed Denitrogenation Reaction of 1,2,3-Benzotriazin-4(3H)-ones Incorporating Isocyanides
    Miura, Tomoya
    Nishida, Yui
    Morimoto, Masao
    Yamauchi, Motoshi
    Murakami, Masahiro
    ORGANIC LETTERS, 2011, 13 (06) : 1429 - 1431
12345