Synthesis of 5-substituted-1H-tetrazoles by lemon juice as a homogeneous and natural catalyst under green reaction conditions

被引:1
|
作者
Valipour, Mohammad [1 ]
Habibzadeh, Setareh [1 ]
Taherimehr, Masoumeh [1 ]
机构
[1] Babol Noshirvani Univ Technol, Fac Sci, Dept Chem, Babol, Iran
关键词
Green synthesis; 5-Substituted-1H-tetrazoles; Cycloaddition reaction; Lemon juice (LJ); SOLVENT-FREE SYNTHESIS; 5-SUBSTITUTED; 1H-TETRAZOLES; REUSABLE NANOCATALYST; TETRAZOLES; EFFICIENT; CHEMISTRY; NITRILES; COMPLEX;
D O I
10.1016/j.jics.2024.101382
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Tetrazole, as a heterocyclic compound, exhibits a wide spectrum of applications in various industries. This research focuses on utilizing a natural catalyst in the synthesis of tetrazole derivatives. Leveraging the acidic nature of lemon juice (LJ), we employed it as a potential catalyst in the synthesis of 5-substituted-1H-tetrazole. LJ would act as the reaction medium as well. This synthesis involves the cycloaddition reaction (3 + 2) of sodium azide to benzonitrile under solvent-free conditions. Optimization of the reaction conditions including temperature, reaction time, and solvent type was tuned towards the highest yield considering the mild reaction time. The best product yield (97 %) was obtained at 90 degrees C, 40 min, in the absence of additional solvent. Various benzonitrile derivatives were examined at the optimized reaction condition.
引用
收藏
页数:6
相关论文
共 50 条
  • [1] A versatile and an efficient synthesis of 5-substituted-1H-tetrazoles
    Reddy, Madhusudana
    Gowd, Muthukur Bhoje
    Pasha, Mohamed Afzal
    JOURNAL OF CHEMICAL SCIENCES, 2011, 123 (01) : 75 - 79
  • [2] A versatile and an efficient synthesis of 5-substituted-1H-tetrazoles
    Gowd M.R.M.B.
    Pasha M.A.
    Journal of Chemical Sciences, 2011, 123 (1) : 75 - 79
  • [3] A Novel Approach for the Synthesis of 5-Substituted-1H-tetrazoles
    Akhlaghinia, Batool
    Rezazadeh, Soodabeh
    JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2012, 23 (12) : 2197 - +
  • [4] In search for an efficient catalyst for azide-nitrile cycloadditions: The synthesis of 5-substituted-1H-tetrazoles under batch and continuous flow conditions
    Kappe, C. Oliver
    Cantillo, David
    Gutmann, Bernhard
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [5] Diisopropylethylammonium acetate (DIPEAc): An efficient and recyclable catalyst for the rapid synthesis of 5-substituted-1H-tetrazoles
    Bhosle, Manisha R.
    Shaikh, Dastgir S.
    Khillare, Lalit D.
    Deshmukh, Amarsinh R.
    Mane, Ramrao A.
    SYNTHETIC COMMUNICATIONS, 2017, 47 (07) : 695 - 703
  • [6] A rapid metal free synthesis of 5-substituted-1H-tetrazoles using cuttlebone as a natural high effective and low cost heterogeneous catalyst
    Ghodsinia, Sara S. E.
    Akhlaghinia, Batool
    RSC ADVANCES, 2015, 5 (62): : 49849 - 49860
  • [7] TRANSITION-METAL COMPLEXES OF 5-SUBSTITUTED-1H-TETRAZOLES
    RAO, NSVS
    GANORKAR, MC
    MURALI, BKM
    RAMASWAMY, CP
    BULLETIN DE L ACADEMIE POLONAISE DES SCIENCES-SERIE DES SCIENCES CHIMIQUES, 1979, 27 (01): : 21 - 28
  • [8] The mineral alum: an effective and low-cost heterogeneous catalyst for the successful synthesis of 5-substituted-1H-tetrazoles
    Karimian, Azam
    Emarloo, Nahid
    Salari, Samira
    INORGANIC AND NANO-METAL CHEMISTRY, 2021, 51 (01) : 91 - 100
  • [9] A practical multigram-scale method for the green synthesis of 5-substituted-1H-tetrazoles in deep eutectic solvent
    Xiong, Xingquan
    Yi, Chao
    Liao, Xu
    Lai, Shilin
    TETRAHEDRON LETTERS, 2019, 60 (05) : 402 - 406
  • [10] Nano TiO2-H3BO3 as an efficient and recycable catalyst for the synthesis of 5-substituted-1H-tetrazoles
    Abrishami, Fatemeh
    Ebrahimikia, Maryam
    Rafiee, Fatemeh
    IRANIAN JOURNAL OF CATALYSIS, 2018, 8 (02): : 103 - 111