Visible-light-promoted three-component cycloaddition reaction: synthesis of 4-functionalized 1,5-disubstituted 1,2,3-triazoles

被引：8
|
作者：
Kumar, Atul [1 ]
Kumar, Navaneet [1 ,2 ]
Bhadoria, Deepak [1 ,2 ]
机构：
[1] CSIR Cent Drug Res Inst, Med & Proc Chem Div, Sect 10,Sitapur Rd,POB 173 Lucknow, Lucknow 226031, Uttar Pradesh, India
[2] Acad Sci & Innovat Res, Ghaziabad 201002, India
来源：
GREEN CHEMISTRY | 2021年 / 23卷 / 20期
关键词：
AZIDE-ALKYNE CYCLOADDITION; REGIOSELECTIVE SYNTHESIS; CLICK CHEMISTRY; 1,3-DIPOLAR CYCLOADDITIONS; CATALYZED CYCLOADDITION; TERMINAL ALKYNES; DIRECT ACCESS; IODINE; CYCLIZATION; SULFONES;
D O I：
10.1039/d1gc02328d
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The first visible-light promoted and photocatalyst-free three-component reaction protocol has been developed to synthesize 4-functionalized 1,5-disubstituted 1,2,3-triazoles from terminal alkynes, aryl azides, and arylsulfinic acid sodium salts or arylsulfonyl hydrazides in an aqueous medium at room temperature. Notably, the reaction proceeds seamlessly without using any transition-metal catalysts, ligands, or photocatalysts, and also reduces chemical waste. It also features an easy operation procedure, high regioselectivity, scalability, a broad substrate scope, mild reaction conditions, and good functional group tolerance.
引用
收藏
页码：7987 / 7995
页数：9
相关论文
共 50 条
  • [1] An Organocatalytic Regiospecific Synthesis of 1,5-Disubstituted 4-Thio-1,2,3-triazoles and 1,5-Disubstituted 1,2,3-Triazoles
    Ramachary, Dhevalapally B.
    Krishna, Patoju M.
    Gujral, Jagjeet
    Reddy, G. Surendra
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (47) : 16775 - 16780
  • [2] Base-Promoted Regiospecific Synthesis of Fully Substituted 1,2,3-Triazoles and 1,5-Disubstituted 1,2,3-Triazoles
    Zhang, Xueying
    Cui, Xue
    Wang, Wei
    Zeng, Tingting
    Wang, Yan
    Tan, Yinfeng
    Liu, Dongyan
    Wang, Xuesong
    Li, Youbin
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 9 (12) : 2176 - 2183
  • [3] Metal-Free Synthesis of 1,5-Disubstituted 1,2,3-Triazoles
    Bubyrev, Andrey
    Malkova, Ksenia
    Kantin, Grigory
    Dar'in, Dmitry
    Krasavin, Mikhail
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (23): : 17516 - 17522
  • [4] Metal-Free Synthesis of 1,5-Disubstituted 1,2,3-Triazoles
    N. T. Pokhodylo
    M. A. Tupychak
    M. D. Obushak
    Russian Journal of Organic Chemistry, 2022, 58 : 209 - 218
  • [5] Metal-Free Synthesis of 1,5-Disubstituted 1,2,3-Triazoles
    Pokhodylo, N. T.
    Tupychak, M. A.
    Obushak, M. D.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 58 (02) : 209 - 218
  • [6] Enzyme-Catalyzed Regioselective Synthesis of 4-Hetero-Functionalized 1,5-Disubstituted 1,2,3-Triazoles
    Kumar, Navaneet
    Kumar, Atul
    ORGANIC LETTERS, 2024, 26 (36) : 7514 - 7519
  • [7] Ionic Liquid-Phase Synthesis of 1,5-Disubstituted 1,2,3-Triazoles
    Koguchi, Shinichi
    Izawa, Kazuki
    ACS COMBINATORIAL SCIENCE, 2014, 16 (08) : 381 - 385
  • [8] An efficient synthesis of 4,5-disubstituted 1,2,3-triazoles by three-component reaction between sodium azide, ethyl cyanoacetate or malonitrile and arylglyoxals
    Derranji, Akram Ranjbar
    Anary-Abbasinejad, Mohammad
    SYNTHETIC COMMUNICATIONS, 2024, 54 (06) : 471 - 477
  • [9] A Metal-Free Multicomponent Cascade Reaction for the Regiospecific Synthesis of 1,5-Disubstituted 1,2,3-Triazoles
    Cheng, Guolin
    Zeng, Xiaobao
    Shen, Jinhai
    Wang, Xuesong
    Cui, Xiuling
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (50) : 13265 - 13268
  • [10] Potassium tert-Butoxide Promoted Cycloaddition Reaction for the Synthesis of 1,5-Disubstituted 1,2,3-Triazoles from Aromatic Azides and Trimethylsilyl-Protected Alkynes
    Wu, Luyong
    Chen, Yuxue
    Tang, Mi
    Song, Xinming
    Chen, Guangying
    Song, Xiaoping
    Lin, Qiang
    SYNLETT, 2012, (10) : 1529 - 1533
12345