Alkyl Propiolates Participated [3+2] Annulation for the Switchable Synthesis of 1,5-and 1,4-Disubstituted 1,2,3-Triazoles Containing Ester Side Chain

被引:28
作者
Cao, Shuo [1 ]
Liu, Yunyun [1 ]
Hu, Changfeng [2 ]
Wen, Chengping [2 ]
Wan, Jie-Ping [1 ]
机构
[1] Jiangxi Normal Univ, Coll Chem & Chem Engn, Nanchang 330022, Jiangxi, Peoples R China
[2] Zhejiang Chinese Med Univ, Coll Basic Med Sci, Hangzhou 310053, Zhejiang, Peoples R China
基金
中国国家自然科学基金;
关键词
alkyl propiolate; annulation; enamine activation; switchable; 1,2,3-triazoles; METAL-FREE; 1,5-DISUBSTITUTED 1,2,3-TRIAZOLES; REGIOSELECTIVE SYNTHESIS; 1,4,5-TRISUBSTITUTED 1,2,3-TRIAZOLES; 1,4,5-SUBSTITUTED 1,2,3-TRIAZOLES; SUBSTITUTED 1,2,3-TRIAZOLES; MULTICOMPONENT REACTIONS; REGIOSPECIFIC SYNTHESIS; CYCLOADDITION REACTIONS; PROMOTED SYNTHESIS;
D O I
10.1002/cctc.201801366
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
By means of a featured enamine activation, the alkyl propiolates have been successfully employed in the [3+2] annulation for the synthesis of 1,2,3-triazoles. The synthesis of both 1,4- as well as the hardly available 1,5-disubstituted 1,2,3-triazoles can be selectively accessed by using tosyl azide and tosyl hydrazine as nitrogen source, respectively.
引用
收藏
页码:5021 / 5025
页数:5
相关论文
共 56 条
  • [1] Click Chemistry: 1,2,3-Triazoles as Pharmacophores
    Agalave, Sandip G.
    Maujan, Suleman R.
    Pore, Vandana S.
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (10) : 2696 - 2718
  • [2] Metal-free [3+2] cycloaddition of azides with Tf2C=CH2 for the regioselective preparation of elusive 4-(trifluoromethylsulfonyl)-1,2,3-triazoles
    Alcaide, Benito
    Almendros, Pedro
    Lazaro-Milla, Carlos
    [J]. CHEMICAL COMMUNICATIONS, 2015, 51 (32) : 6992 - 6995
  • [3] An efficient one-pot strategy for the highly regioselective metal-free synthesis of 1,4-disubstituted-1,2,3-triazoles
    Ali, Akbar
    Correa, Arlene G.
    Alves, Diego
    Zukerman-Schpector, Julio
    Westermann, Bernhard
    Ferreira, Marco A. B.
    Paixao, Marcio W.
    [J]. CHEMICAL COMMUNICATIONS, 2014, 50 (80) : 11926 - 11929
  • [4] Aerobic Oxidative Cycloaddition of α-Chlorotosylhydrazones with Arylamines: General Chemoselective Construction of 1,4-Disubstituted and 1,5-Disubstituted 1,2,3-Triazoles under Metal-Free and Azide-Free Conditions
    Bai, Hui-Wen
    Cai, Zhong-Jian
    Wang, Shun-Yi
    Ji, Shun-Jun
    [J]. ORGANIC LETTERS, 2015, 17 (12) : 2898 - 2901
  • [5] The Rich Chemistry Resulting from the 1,3-Dipolar Cycloaddition Reactions of Enamines and Azides
    Bakulev, Vasiliy A.
    Beryozkina, Tetyana
    Thomas, Joice
    Dehaen, Wim
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (03) : 262 - 294
  • [6] Ruthenium-catalyzed azide-alkyne cycloaddition: Scope and mechanism
    Boren, Brant C.
    Narayan, Sridhar
    Rasmussen, Lars K.
    Zhang, Li
    Zhao, Haitao
    Lin, Zhenyang
    Jia, Guochen
    Fokin, Valery V.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (28) : 8923 - 8930
  • [7] Copper-Catalyzed [3+2] Cycloaddition/Oxidation Reactions between Nitro-olefins and Organic Azides: Highly Regioselective Synthesis of NO2-Substituted 1,2,3-Triazoles
    Chen, Yunfeng
    Nie, Gang
    Zhang, Qi
    Ma, Shan
    Li, Huan
    Hu, Qinquan
    [J]. ORGANIC LETTERS, 2015, 17 (05) : 1118 - 1121
  • [8] Recent Developments in Azide-Free Synthesis of 1,2,3-Triazoles
    Chen, Zhengkai
    Cao, Gangjian
    Song, Jinyu
    Ren, Hongjun
    [J]. CHINESE JOURNAL OF CHEMISTRY, 2017, 35 (12) : 1797 - 1807
  • [9] Recent Advances in Multicomponent Synthesis of 1,4,5-Trisubstituted 1,2,3-Triazoles
    Chen, Zhengkai
    Liu, Zhubo
    Cao, Gangjian
    Li, Hongli
    Ren, Hongjun
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (02) : 202 - 224
  • [10] Metal-Free C-N- and N-N-Bond Formation: Synthesis of 1,2,3-Triazoles from Ketones, N-Tosylhydrazines, and Amines in One Pot
    Chen, Zhengkai
    Yan, Qiangqiang
    Liu, Zhanxiang
    Zhang, Yuhong
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (52) : 17635 - 17639