Transition-Metal-Free Synthesis of Indolizines from Electron-Deficient Alkenes via One-Pot Reaction Using TEMPO as an Oxidant

被引:38
|
作者
Shi, Fei [1 ,2 ]
Zhang, Yu [1 ,2 ]
Lu, Zhaole [2 ]
Zhu, Xiaolei [2 ]
Kan, Weiqiu [2 ]
Wang, Xiang [2 ]
Hu, Huayou [1 ,2 ]
机构
[1] Ningxia Univ, Sch Chem & Chem Engn, Yinchuan 750021, Peoples R China
[2] Huaiyin Normal Univ, Sch Chem & Chem Engn, Jiangsu Key Lab Chem Low Dimens Mat, Huaian 223300, Peoples R China
来源
SYNTHESIS-STUTTGART | 2016年 / 48卷 / 03期
关键词
N-ylide; alkenes; 1,3-dipolar cycloaddition; tandem reaction; dehydrogenation; AEROBIC OXIDATION; MOLECULAR-OXYGEN; CARBON-CARBON; BOND-CLEAVAGE; C-C; DERIVATIVES; ALCOHOLS; FLUORESCENCE; INHIBITORS; EQUIVALENT;
D O I
10.1055/s-0035-1560973
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A one-pot method for the synthesis of multisubstituted indolizines from alpha-halo carbonyl compounds, pyridines, and electron-deficient alkenes is reported. The oxidative dehydrogenation reaction takes place under transition-metal-free conditions using TEMPO as an oxidant. This protocol uses ready available starting materials in a convenient procedure under mild reaction conditions.
引用
收藏
页码:413 / 420
页数:8
相关论文
共 50 条
  • [1] Synthesis of 3-Unsubstituted Indolizines from Electron Deficient Alkenes under Transition Metal Free Conditions
    Hu, Huayou
    Li, Guodong
    Gu, Ning
    Ii, Min
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2016, 36 (02) : 330 - 335
  • [2] One-Pot Transition-Metal-Free Synthesis of Weinreb Amides Directly from Carboxylic Acids
    Niu, Teng
    Wang, Ke-Hu
    Huang, Danfeng
    Xu, Changming
    Su, Yingpeng
    Hu, Yulai
    Fu, Ying
    SYNTHESIS-STUTTGART, 2014, 46 (03): : 320 - 330
  • [3] Transition-metal-free synthesis of pyrimidines from lignin β-O-4 segments via a one-pot multi-component reaction
    Zhang, Bo
    Guo, Tenglong
    Li, Zhewei
    Kuhn, Fritz E.
    Lei, Ming
    Zhao, Zongbao K.
    Xiao, Jianliang
    Zhang, Jian
    Xu, Dezhu
    Zhang, Tao
    Li, Changzhi
    NATURE COMMUNICATIONS, 2022, 13 (01)
  • [4] Metal free one-pot synthesis of α-ketoamides from terminal alkenes
    Dutta, Sayan
    Kotha, Surya Srinivas
    Sekar, Govindasamy
    RSC ADVANCES, 2015, 5 (58) : 47265 - 47269
  • [5] A One-Pot Domino Reaction for the Synthesis of 3-Arylindolizines from Pyridines, Benzyl Halides, and Dihalide-Substituted Electron-Deficient Alkenes
    Hu, Huayou
    Shi, Kunbo
    Hou, Rongrong
    Zhang, Zaichao
    Zhu, Yulan
    Zhou, Jianfeng
    SYNTHESIS-STUTTGART, 2010, (23): : 4007 - 4014
  • [6] Transition-Metal-Free Synthesis of Conjugated Polymers from Bis-Grignard Reagents by Using TEMPO as Oxidant
    Maji, Modhu Sudan
    Pfeifer, Thorben
    Studer, Armido
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (20) : 5872 - 5875
  • [7] Transition-Metal-Free One-Pot Synthesis of Fused Benzofuranamines and Benzo[b]thiophenamines
    Liu, Ran
    Lv, Lili
    Yang, Bingchuan
    Gu, Ziyi
    Li, Chenglong
    Lv, Xueyan
    Ding, Chengcheng
    Huang, Xianqiang
    Yuan, Dong
    Liu, Tao
    Chen, Xuexiang
    MOLECULES, 2023, 28 (23):
  • [8] Transition metal-free one-pot double C-H functionalization of quinolines with disubstituted electron-deficient acetylenes
    Trofimov, B. A.
    Belyaeva, K. V.
    Nikitina, L. P.
    Mal'kina, A. G.
    Afonin, A. V.
    Ushakov, I. A.
    Vashchenko, A. V.
    CHEMICAL COMMUNICATIONS, 2018, 54 (46) : 5863 - 5866
  • [9] Acetylene as a Driving and Organizing Molecule in One-Pot Transition-Metal-Free Synthesis of Furans using Chalcones and their Analogues
    Trofimov, Boris A.
    Bidusenko, Ivan A.
    Schmidt, Elena Yu.
    Ushakov, Igor' A.
    Vashchenko, Alexander V.
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (06) : 707 - 711
  • [10] One-Pot Transition-Metal-Free Synthesis of Dibenzo[b,f]oxepins from 2-Halobenzaldehydes
    Choi, Young Lok
    Lim, Hye Sun
    Lim, Hwan Jung
    Hee, Jung-Nyoung
    ORGANIC LETTERS, 2012, 14 (19) : 5102 - 5105