An efficient synthesis of 4,5-disubstituted 1,2,3-triazoles by three-component reaction between sodium azide, ethyl cyanoacetate or malonitrile and arylglyoxals

被引:0
|
作者
Derranji, Akram Ranjbar [1 ]
Anary-Abbasinejad, Mohammad [1 ]
机构
[1] Vali e Asr Univ Rafsanjan, Dept Chem, Rafsanjan, Iran
关键词
Ethyl cyanoacetate; malononitrile; sodium azide; triazole; three-component reaction; ONE-POT SYNTHESIS; TANDEM;
D O I
10.1080/00397911.2024.2312509
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Three-component reaction between sodium azide, ethyl cyanoacetate or malonitrile and arylglyoxals afforded 4,5-disubstituted 1,2,3-triazole derivatives in high yields. All reactions were conducted in ethanol as an environmentally benign solvent at room temperature without using any catalyst or modifier. Stable solid products were easily isolated and purified by washing with water and diethyl ether. The structures of the compounds were proved by H-1 and C-13 NMR and IR spectral and elemental analysis data. [GRAPHICS] .
引用
收藏
页码:471 / 477
页数:7
相关论文
共 50 条
  • [21] A Metal-Free Three-Component Reaction for the Regioselective Synthesis of 1,4,5-Trisubstituted 1,2,3-Triazoles
    Thomas, Joice
    John, Jubi
    Parekh, Nikita
    Dehaen, Wim
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (38) : 10155 - 10159
  • [22] Synthesis and Antitubercular Activity of 4,5-Disubstituted N1-(5′-deoxythymidin-5′-yl)-1,2,3-triazoles
    Kumar, Rajesh
    Bimal, Devla
    Kavita
    Kumar, Manish
    Mathur, Divya
    Maity, Jyotirmoy
    Singh, Sunil K.
    Thirumal, M.
    Prasad, Ashok K.
    CHEMISTRYSELECT, 2020, 5 (28): : 8839 - 8845
  • [23] Ionic Liquid-Phase Synthesis of 1,5-Disubstituted 1,2,3-Triazoles
    Koguchi, Shinichi
    Izawa, Kazuki
    ACS COMBINATORIAL SCIENCE, 2014, 16 (08) : 381 - 385
  • [24] Three-Component Synthesis of 1,4-Disubstituted 1,2,3-Triazoles using a Novel and Efficient Nano Alumina Based Cu(II) Catalyst
    Khoshnoud, Amin
    Pourali, Ali Reza
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2021, 53 (06) : 509 - 517
  • [25] Wheel-shaped copper containing polyoxotungstate as an efficient catalyst in the three-component synthesis of 1,2,3-triazoles
    Jalilian, Fariba
    Yadollahi, Bahram
    Tangestaninejad, Shahram
    Rudbari, Hadi Amiri
    RSC ADVANCES, 2016, 6 (17): : 13609 - 13613
  • [26] A General Proline-Catalyzed Synthesis of 4,5-Disubstituted N-Sulfonyl-1,2,3-Triazoles from 1,3-Dicarbonyl Compounds and Sulfonyl Azide
    Rajasekar, Shanmugam
    Anbarasan, Pazhamalai
    CHEMISTRY-AN ASIAN JOURNAL, 2019, 14 (24) : 4563 - 4567
  • [27] THE SYNTHESIS OF 1,2,3-TRIAZOLES AND AZIRIDINES USING 2-(4-PYRIDYL)ETHYL AZIDE
    KATRITZKY, AR
    TAKAHASHI, I
    MARSON, CM
    SCRIVEN, EFV
    CHEMICA SCRIPTA, 1988, 28 (02): : 149 - 155
  • [28] 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
  • [29] An Efficient One-pot Three-component Reaction to Produce 1,4-Disubstituted-1,2,3-triazoles Catalyzed by a Dicopper-substituted Silicotungstate
    Yamaguchi, Kazuya
    Kotani, Miyuki
    Kamata, Keigo
    Mizuno, Noritaka
    CHEMISTRY LETTERS, 2008, 37 (12) : 1258 - 1259
  • [30] Acetic acid-catalyzed synthesis of 1,5-disubstituted 1,2,3-triazoles under azide-free conditions
    Li, Jiuling
    Jia, Xinyu
    Yang, Qiangguo
    Guo, Jiakang
    Ren, Qianhui
    Liu, Taichen
    Wei, Kai
    Kang, Zhenghui
    ORGANIC CHEMISTRY FRONTIERS, 2025, 12 (04): : 1238 - 1243