Application of a functionalized mesoporous silica catalyst to the synthesis of tetrazoles

被引：23
作者：
Chermahini, Alireza Najafi [1 ]
Omran, Masoud Khani [1 ]
Dabbagh, Hossein A. [1 ]
Mohammadnezhad, Gholamhossein [1 ]
Teimouri, Abbas [2 ]
机构：
[1] Isfahan Univ Technol, Dept Chem, Esfahan 8415683111, Iran
[2] Payame Noor Univ PNU, Dept Chem, Tehran 193954697, Iran
来源：
NEW JOURNAL OF CHEMISTRY | 2015年 / 39卷 / 06期
关键词：
EFFICIENT HETEROGENEOUS CATALYST; 5-SUBSTITUTED; 1H-TETRAZOLES; 3+2 CYCLOADDITION; LEWIS-ACID; NITRILES; MCM-41; DERIVATIVES; AZIDE; SALTS;
D O I：
10.1039/c5nj00211g
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
In the present study, well ordered MCM-41 was synthesized and functionalized with benzyl group and subsequently sulfonated with chlorosulfonic acid. The functionalized catalyst (MCMBSA) was characterized by XRD, TGA, FTIR, TEM, BET, and SEM. 5-Aryl-1H-tetrazoles were synthesized by the reaction of the corresponding aryl nitriles and sodium azide catalyzed by MCMBSA. The mole ratio of nitrile to sodium azide, the amount of catalyst, reaction times, and solvent type were optimized. The MCMBSA catalyst was more effective than the catalyst obtained from the direct sulfonation of MCM-41. The versatility of the method was investigated by using various nitriles, which showed reasonable yields of tetrazoles. The regeneration and reusability of catalyst was also examined.
引用
收藏
页码：4814 / 4820
页数：7
相关论文
共 52 条
  • [1] Heavy metals removal from electroplating wastewater by aminopropyl-Si MCM-41
    Algarra, M
    Jiménez, MV
    Rodríguez-Castellón, E
    Jiménez-López, A
    Jiménez-Jiménez, J
    [J]. CHEMOSPHERE, 2005, 59 (06) : 779 - 786
  • [2] 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
  • [3] Iron Salts in the Catalyzed Synthesis of 5-Substituted 1H-Tetrazoles
    Bonnamour, Julien
    Bolm, Carsten
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (18) : 4543 - 4545
  • [4] Cu2(OTf)2-catalyzed and microwave-controlled preparation of tetrazoles from nitriles and organic azides under mild, safe conditions
    Bosch, Lluis
    Vilarrasa, Jaume
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (21) : 3926 - 3930
  • [5] Burger A, 1991, Prog Drug Res, V37, P287
  • [6] Butler R N, 1996, COMPREHENSIVE HETERO, V4, P674
  • [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] Clay-Catalyzed Synthesis of 5-Substituent 1-H-Tetrazoles
    Chermahini, Alireza Najafi
    Teimouri, Abbas
    Momenbeik, Fariborz
    Zarei, Amin
    Dalirnasab, Zeinab
    Ghaedi, Aseyeh
    Roosta, Mostafa
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2010, 47 (04) : 913 - 922
  • [9] Preparation of 5-substituted 1H-tetrazoles from nitriles in water
    Demko, ZP
    Sharpless, KB
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (24) : 7945 - 7950
  • [10] Improved Synthesis of 5-Substituted 1H-Tetrazoles via the [3+2] Cycloaddition of Nitriles and Sodium Azide Catalyzed by Silica Sulfuric Acid
    Du, Zhenting
    Si, Changmei
    Li, Youqiang
    Wang, Yin
    Lu, Jing
    [J]. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2012, 13 (04): : 4696 - 4703
123456