Three-Component Reaction o f 3-Arylidene-3H-Indolium Salts, Isocyanides, and Alcohols

被引：4
|
作者：
Golantsov, Nikita E. [1 ]
Nguyen, Hung M. [1 ]
Golubenkova, Alexandra S. [1 ]
Varlamov, Alexey V. [1 ]
Van der Eycken, Erik V. [1 ,2 ]
Voskressensky, Leonid G. [1 ]
机构：
[1] RUDN Univ, Peoples Friendship Univ Russia, Fac Sci, Dept Organ Chem, Moscow, Russia
[2] Katholieke Univ Leuven, Univ Leuven, Dept Chem, LOMAC, Leuven, Belgium
来源：
FRONTIERS IN CHEMISTRY | 2019年 / 7卷
基金：
俄罗斯科学基金会;
关键词：
multicomponent reactions; isocyanides; indoleninium ions; aryl(indol-3-yl)methylium ions; imidates; MULTICOMPONENT REACTIONS SYNTHESIS; MICHAEL ADDITION; CYCLOADDITION; EFFICIENT; INDOLES; TOOL;
D O I：
10.3389/fchem.2019.00345
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A novel isocyanide-based multicomponent synthesis of alkyl aryl(indol-3-yl)acetimidates has been established. Starting from aryl(indol-3-yl)methylium tetrafluoroborates, aromatic isocyanides and alcohols, the imidates were obtained in moderate to very good yields. Consecutive four-component synthesis of the above mentioned imidates from N-alkylindoles, aromatic aldehydes, aromatic isocyanides and alcohols was also proposed. In addition, it was shown that in the presence of water, aryl(indol-3-yl)methylium tetrafluoroborates reacted with isocyanides to furnish aryl(indol-3-yl)acetamides.
引用
收藏
页数：14
相关论文
共 50 条
  • [21] Three-Component Mannich Reaction Catalyzed by Mesostructured Cellular Foam Silica Immobilized H3PW12O40
    Dong, Hao
    Fan, Qinzhen
    Luo, Guanwei
    Zhang, Tengfei
    Yang, Hongyuan
    Liu, Qing
    Zhao, Guoming
    Yang, Jing
    CHEMISTRYSELECT, 2019, 4 (28): : 8338 - 8343
  • [22] Simple and efficient synthesis of pyrrolo[3,2-f]quinoxaline derivatives via three-component reaction
    Wan, Dan-Dan
    Qian, Yu-heng
    Liu, Jia-Yan
    Chen, Dong-Sheng
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2024, 61 (07) : 1141 - 1149
  • [23] Photoinduced Three-Component Reaction: A Convenient Access to 3-Arylacetals or 3-Arylketals
    Lazzaroni, Simone
    Protti, Stefano
    Fagnoni, Maurizio
    Albini, Angelo
    ORGANIC LETTERS, 2009, 11 (02) : 349 - 352
  • [24] A new synthesis of 7H-pyrrolo[3,2-f]quinoxaline derivatives by a one-pot, three-component reaction
    Wang, Xue
    Li, Ji
    Liu, Jia-Yan
    Chen, Dong-Sheng
    JOURNAL OF CHEMICAL SCIENCES, 2024, 136 (04)
  • [25] Efficient three-component synthesis of tetrahydrothieno[3,2-f]quinolines
    Van Snick, Wim
    Parchina, Anastasia
    Dehaen, Wim
    TETRAHEDRON, 2011, 67 (23) : 4179 - 4184
  • [26] Phototriggered Self-Catalyzed Three-Component Minisci Reaction: A Route to β-C(sp3) Heteroarylated Alcohols/Ethers
    Wang, Chaodong
    Song, Shengjie
    Chen, Zhi
    Shen, Dengjian
    Wang, Zhenhui
    Zhou, Jiadi
    Guo, Jingjing
    Li, Jianjun
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (24): : 16794 - 16806
  • [27] Palladium-catalyzed three-component reaction for the synthesis of 3,3-disubstituted allylic alcohols with regio- and stereoselectivity
    Hu, Gang
    Wang, Jingtao
    Li, Zefei
    Liu, Yajing
    Gong, Ping
    NEW JOURNAL OF CHEMISTRY, 2018, 42 (03) : 1736 - 1739
  • [28] Three-Component Radical Cascade Reaction of Quinoxalinones, Alkenes and AgSCF3
    Peng, Sha
    Xie, Long-Yong
    Yang, Luo
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (19) : 3328 - 3334
  • [29] A new three-component cascade reaction to yield 3-spirocyclopropanated β-lactams
    Zanobini, A
    Brandi, A
    de Meijere, A
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (05) : 1251 - 1255
  • [30] Synthesis of Iodine-Substituted Quinolines, Quinolinium Salts, and Isoquinolinium Salts via a Three-Component Tandem Reaction of Aryl Azides, Propargylic Alcohols, and Iodine
    Wu, Yunjun
    Shao, Min
    Feng, Zhijun
    Gu, Xiaoxia
    Hong, Yi
    Cui, Qiaoyu
    Ren, Lianbing
    Wang, Shaoyin
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (01) : 76 - 82
12345