An enolate-mediated regioselective synthesis of 1,2,3-triazoles via azide-aldehydes or ketones [3+2]-cycloaddition reactions in aqueous phase

被引：8
作者：
Tripathi, Anupam [1 ,2 ]
Rode, Chandrashekhar, V [3 ]
Llop, Jordi [4 ]
Chavan, Subhash P. [1 ,2 ]
Joshi, Sameer M. [1 ,2 ,5 ]
机构：
[1] CSIR, Div Organ Chem, Natl Chem Lab, Pune 411008, Maharashtra, India
[2] Acad Sci & Innovat Res AcSIR, New Delhi 110025, India
[3] Natl Chem Lab, Chem Engn & Proc Dev Div, Dr HomiBhabha Rd, Pune 411008, Maharashtra, India
[4] CIC biomaGUNE, Radiochem & Nucl Imaging, Paseo Miramon 182, San Sebastian 20014, Spain
[5] Wayne State Univ, Dept Oncol, Detroit, MI 48202 USA
来源：
TETRAHEDRON LETTERS | 2020年 / 61卷 / 13期
关键词：
Click chemistry; Azides plus aldehydes or ketones; Triazoles; Water; 1,3-DIPOLAR CYCLOADDITION REACTION; HIGH-YIELDING SYNTHESIS; DIRECT ACCESS; 1,5-DISUBSTITUTED 1,2,3-TRIAZOLES; AZIDOPHENYL ARYLSELENIDES; ORGANOCATALYTIC SYNTHESIS; REGIOSPECIFIC SYNTHESIS; ALKYNE CYCLOADDITION; LIGATION; AMIDES;
D O I：
10.1016/j.tetlet.2020.151662
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A synthetic route for the direct conversion of arylazides into the corresponding trizoles via phase transfer catalyst-assisted [3+2] cycloaddition reaction under basic conditions in aqueous medium is reported. This synthetic methodology, which offers high yields and excellent regioselectivity for varieties of triazoles at 100 degrees C for 24 h-48 h and this 'greener' synthesis constitutes an alternative to the previously reported well established click reactions. Published by Elsevier Ltd.
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页数：5
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共 59 条
  • [51] Tome A.C., 2004, Sci. Synth, V13, P415, DOI DOI 10.1055/S0S-SD-013-00626
  • [52] Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides
    Tornoe, CW
    Christensen, C
    Meldal, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (09) : 3057 - 3064
  • [53] Amine-Catalyzed [3+2] Huisgen Cycloaddition Strategy for the Efficient Assembly of Highly Substituted 1,2,3-Triazoles
    Wang, Lei
    Peng, Shiyong
    Danence, Lee Jin Tu
    Gao, Yaojun
    Wang, Jian
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (19) : 6088 - 6093
  • [54] Organocatalytic 1,3-dipolar [3+3] cycloaddition reaction of 1,2-cyclohexanedione with azides: direct access to highly substituted 1,2,3-triazoles
    Xu, Xianhong
    Shi, Zhenyan
    Li, Wenjun
    [J]. NEW JOURNAL OF CHEMISTRY, 2016, 40 (08) : 6559 - 6563
  • [55] Transition metal free oxygenation of 8-aminoquinoline amides in water
    Yao, Xinghui
    Weng, Xin
    Wang, Kaixuan
    Xiang, Haifeng
    Zhou, Xiangge
    [J]. GREEN CHEMISTRY, 2018, 20 (11) : 2472 - 2476
  • [56] Organocatalytic 1,3-dipolar cycloaddition reactions of ketones and azides with water as a solvent
    Yeung, Dwun Kit Jonathan
    Gao, Tao
    Huang, Jiayao
    Sun, Shaofa
    Guo, Haibing
    Wang, Jian
    [J]. GREEN CHEMISTRY, 2013, 15 (09) : 2384 - 2388
  • [57] Ruthenium-catalyzed cycloaddition of alkynes and organic azides
    Zhang, L
    Chen, XG
    Xue, P
    Sun, HHY
    Williams, ID
    Sharpless, KB
    Fokin, VV
    Jia, GC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (46) : 15998 - 15999
  • [58] Enolate-mediated 1,3-dipolar cycloaddition reaction of β-functionalized ketones with nitrile oxides: direct access to 3,4,5-trisubstituted isoxazoles
    Zhou, Xiao
    Xu, Xianhong
    Shi, Zhenyan
    Liu, Kun
    Gao, Hua
    Li, Wenjun
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (23) : 5246 - 5250
  • [59] Organocatalytic 1,3-Dipolar Cycloaddition Reaction of β-Keto Amides with Azides - Direct Access to 1,4,5-Trisubstituted 1,2,3-Triazole-4-carboxamides
    Zhou, Xiao
    Xu, Xianhong
    Liu, Kun
    Gao, Hua
    Wang, Wei
    Li, Wenjun
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (10) : 1886 - 1890
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