Transition-metal-free synthesis of multisubstituted N-arylindoles via reaction of arynes and α-amino ketones

被引：27
|
作者：
He, Lin [1 ]
Pian, Ji-Xin [1 ]
Shi, Jun-Feng [1 ]
Du, Guang-Fen [1 ]
Dai, Bin [1 ]
机构：
[1] Shihezi Univ, Sch Chem & Chem Engn, Key Lab Green Proc Chem Engn Xinjiang Bingtuan, Shihezi 832000, Xinjiang Uygur, Peoples R China
来源：
TETRAHEDRON | 2014年 / 70卷 / 14期
基金：
中国国家自然科学基金;
关键词：
Indoles; Arynes; Cross-coupling reaction; alpha-Amino ketones; SIMPLE INDOLE ALKALOIDS; EFFICIENT SYNTHESIS; OXIDATIVE CYCLIZATION; BOND; BENZYNE; CONSTRUCTION; AMINATION; ARYLATION; CASCADE;
D O I：
10.1016/j.tet.2014.02.028
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple transition-metal-free protocol for the synthesis of indoles has been developed using aryne cycloaddition. The in situ-generated arynes couple with alpha-amino ketones through a one-step N-arylation-nucleophilic addition process under mild conditions and efficiently produce multi-substituted N-arylindoles. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2400 / 2405
页数：6
相关论文
共 50 条
  • [1] Selective Synthesis of N-Unsubstituted and N-Arylindoles by the Reaction of Arynes with Azirines
    Thangaraj, Manikandan
    Bhojgude, Sachin Suresh
    Jain, Shailja
    Gonnade, Rajesh G.
    Biju, Akkattu T.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (18): : 8604 - 8611
  • [2] A Transition-Metal-Free Synthesis of Multisubstituted Imidazoles
    Wu, Ping
    Zhang, Lutao
    Zhang, Xueguo
    Guo, Xin
    Chen, Baohua
    [J]. CHINESE JOURNAL OF CHEMISTRY, 2016, 34 (04) : 363 - 367
  • [3] Transition-Metal-Free Synthesis of N-Aryl Hydroxamic Acids via Insertion of Arynes
    Zhang, Lanlan
    Geng, Yu
    Jin, Zhong
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (09): : 3542 - 3552
  • [4] Transition-Metal-Free α-Arylation of β-Keto Amides via an Interrupted Insertion Reaction of Arynes
    Mohanan, Kishor
    Coquerel, Yoann
    Rodriguez, Jean
    [J]. ORGANIC LETTERS, 2012, 14 (17) : 4686 - 4689
  • [5] Transition-Metal-Free Synthesis of 2-Arylimidazolones via Cascade Reaction between Arynes and α,α′-Disubstituted α-Isocyanoacetamides
    Gesu, Alessandro
    Pozzoli, Claudio
    Torre, Enza
    Aprile, Silvio
    Pirali, Tracey
    [J]. ORGANIC LETTERS, 2016, 18 (09) : 1992 - 1995
  • [6] Transition-Metal-Free Diarylation of Isocyanates with Arynes
    Jang, Woo Cheol
    Hwang, Dong Wook
    Seo, Jeong Hoon
    Ko, Haye Min
    [J]. TETRAHEDRON LETTERS, 2019, 60 (38)
  • [7] Transition-Metal-Free Coupling Annulation of Arynes with Ketones and Alkynoates: Assembly of Functionalized Naphthalenes
    Shu, Wen-Ming
    Zheng, Kai-Lu
    Ma, Jun-Rui
    Wu, An-Xin
    [J]. ORGANIC LETTERS, 2016, 18 (15) : 3762 - 3765
  • [8] Transition-Metal-Free Cascade Synthesis of 4-Quinolones: Umpolung of Michael Acceptors via Ene Reaction with Arynes
    Reddy, R. Santhosh
    Lagishetti, Chandraiah
    Kiran, I. N. Chaithanya
    You, Hengyao
    He, Yun
    [J]. ORGANIC LETTERS, 2016, 18 (15) : 3818 - 3821
  • [9] Transition-metal-free synthesis of 4-amino isoquinolin-1(2H)-ones via a tandem reaction of arynes and oxazoles
    Liu, Shaojun
    Xie, Pei
    Wu, Leifang
    Zhao, Jixing
    Cai, Zhihua
    He, Lin
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (06): : 1550 - 1555
  • [10] Transition-Metal-Free Oxidative α-C-H Amination of Ketones via a Radical Mechanism: Mild Synthesis of α-Amino Ketones
    Jiang, Qing
    Xu, Bin
    Zhao, An
    Jia, Jing
    Liu, Tian
    Guo, Cancheng
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (18): : 8750 - 8756
12345