1-Disulfo-[2,2-bipyridine]-1,1-diium chloride ionic liquid as an efficient catalyst for the green synthesis of 5-substituted 1 H-tetrazoles

被引:19
作者
Aali, Elaheh [1 ]
Gholizadeh, Mostafa [1 ]
Noroozi-Shad, Nazanin [1 ]
机构
[1] Ferdowsi Univ Mashhad, Fac Sci, Dept Chem, Mashhad, Razavi Khorasan, Iran
关键词
Cycloaddition reaction; 1-Disulfo-[22-bipyridine]-1,1-diium chloride; Ionic liquid; Tetrazoles; 3+2 CYCLOADDITION; 1H-TETRAZOLES; CHEMISTRY; NITRILES; ACID; CONVERSION;
D O I
10.1016/j.molstruc.2021.131289
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
A simple, green and efficient method has been developed for the synthesis of 5-substituted 1H-tetrazole derivatives through [2 + 3] cycloaddition reaction in good to excellent yields between various benzonitriles and sodium azide. For this purpose, 1-disulfo-[2,2-bipyridine]-1,1-diium chloride ([BiPy](HSO3)(2)Cl-2) system as an ionic liquid catalyst have been extended for the construction of these valuable products. This procedure has significant advantages, including using ethylene glycol as a green solvent. The other advantages of this method are inexpensive and ease the preparation of the catalyst, mild reaction conditions, green reaction medium, easy workup, short reaction time, and simple experimental process. (C) 2021 Elsevier B.V. All rights reserved.
引用
收藏
页数:7
相关论文
共 54 条
  • [1] TBAF-Catalyzed synthesis of 5-substituted IH-tetrazoles under solventless conditions
    Amantini, D
    Beleggia, R
    Fringuelli, F
    Pizzo, F
    Vaccaro, L
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (08) : 2896 - 2898
  • [2] Acidic Ionic Liquids
    Amarasekara, Ananda S.
    [J]. CHEMICAL REVIEWS, 2016, 116 (10) : 6133 - 6183
  • [3] Highly Efficient Synthesis of 5-Substituted 1H-Tetrazoles Catalyzed by Cu-Zn Alloy Nanopowder, Conversion into 1,5-and 2,5-Disubstituted Tetrazoles, and Synthesis and NMR Studies of New Tetrazolium Ionic Liquids
    Aridoss, Gopalakrishnan
    Laali, Kenneth K.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (31) : 6343 - 6355
  • [4] Molecular and Crystal Structure of 1-(4-Fluorophenyl)-1,4-Dihydro-1H-Tetrazole-5-Thione and Its Complex with Cadmium(II)
    Askerov, R. K.
    Maharramov, A. M.
    Osmanov, V. K.
    Baranov, E. V.
    Borisova, G. N.
    Dorovatovskii, P. V.
    Khrustalev, V. N.
    Borisov, A. V.
    [J]. JOURNAL OF STRUCTURAL CHEMISTRY, 2018, 59 (07) : 1658 - 1663
  • [5] 1,3-dipolar cycloaddition: Click chemistry for the synthesis of 5-substituted tetrazoles from organoaluminum azides and nitriles
    Aureggi, Valentina
    Sedelmeier, Gottfried
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (44) : 8440 - 8444
  • [6] The Literature of Heterocyclic Chemistry, Part XVI, 2016
    Belen'kii, Leonid I.
    Evdokimenkova, Yulia B.
    [J]. ADVANCES IN HETEROCYCLIC CHEMISTRY, VOL 126, 2018, 126 : 173 - 254
  • [7] Simple and Efficient Synthesis of 5-Substituted 1-H-Tetrazoles Using Metal-Modified Clay Catalysts
    Chermahini, Alireza Najafi
    Teimouri, Abbas
    Moaddeli, Ali
    [J]. HETEROATOM CHEMISTRY, 2011, 22 (02) : 168 - 173
  • [8] Tin-Catalyzed Synthesis of 5-Substituted 1H-Tetrazoles from Nitriles: Homogeneous and Heterogeneous Procedures
    Chretien, Jean-Mathieu
    Kerric, Gaelle
    Zammattio, Francoise
    Galland, Nicolas
    Paris, Michael
    Quintard, Jean-Paul
    Le Grognec, Erwan
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (04) : 747 - 757
  • [9] Green and Sustainable Solvents in Chemical Processes
    Clarke, Coby J.
    Tu, Wei -Chien
    Levers, Oliver
    Brohl, Andreas
    Hallett, Jason P.
    [J]. CHEMICAL REVIEWS, 2018, 118 (02) : 747 - 800
  • [10] tris(2-perfluorohexylethyl) tin azide:: A new reagent for preparation of 5-substituted tetrazoles from nitriles with purification by fluorous organic liquid-liquid extraction
    Curran, DP
    Hadida, S
    Kim, SY
    [J]. TETRAHEDRON, 1999, 55 (29) : 8997 - 9006