Synthesis of 5-Substituted 1H-Tetrazoles from Nitriles and Hydrazoic Acid by Using a Safe and Scalable High-Temperature Microreactor Approach

被引：161
|
作者：
Gutmann, Bernhard [2 ,3 ]
Roduit, Jean-Paul [1 ]
Roberge, Dominique [1 ]
Kappe, C. Oliver [2 ,3 ]
机构：
[1] Lonza AG, Microreactor Technol, CH-3930 Visp, Switzerland
[2] Karl Franzens Univ Graz, CDLMC, A-8010 Graz, Austria
[3] Karl Franzens Univ Graz, Inst Chem, A-8010 Graz, Austria
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 39期
关键词：
cycloaddition; hydrazoic acid; microreactors; process intensification; tetrazoles; POT TANDEM REACTIONS; TETRAZOLE FORMATION; CATALYZED SYNTHESIS; HETEROGENEOUS CATALYST; TRIMETHYLSILYL AZIDE; EFFICIENT SYNTHESIS; DIRECT CONVERSION; ORGANIC NITRILES; AQUEOUS-MEDIA; SODIUM-AZIDE;
D O I：
10.1002/anie.201003733
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Harnessing hydrazoic acid in a microreactor! Tetrazoles have been synthesized in a very efficient manner by using a high-temperature/high-pressure process intensification regime. Despite the toxic and explosive nature of hydrazoic acid, the synthesis was conducted safely in continuous flow format with residence times as short as 2.5 minutes at 260□°C (see picture). © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：7101 / 7105
页数：5
相关论文
共 50 条
  • [11] An efficient synthesis of 5-substituted 1H-tetrazoles catalyzed by graphene
    Qi, Gang
    Zhang, Wenguo
    Dai, Yong
    RESEARCH ON CHEMICAL INTERMEDIATES, 2015, 41 (02) : 1149 - 1155
  • [12] Ammonium acetate mediated synthesis of 5-substituted 1H-tetrazoles
    Patil, Dipak R.
    Deshmukh, Mukesh B.
    Dalal, Dipak S.
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2012, 9 (05) : 799 - 803
  • [13] The synthesis of 5-substituted 1H-tetrazoles in molten tetrabutylammonium bromide
    Xie, Aming
    Cao, Meiping
    Feng, Liandong
    Dong, Wei
    JOURNAL OF CHEMICAL RESEARCH, 2013, (11) : 665 - 667
  • [14] Iron Salts in the Catalyzed Synthesis of 5-Substituted 1H-Tetrazoles
    Bonnamour, Julien
    Bolm, Carsten
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (18) : 4543 - 4545
  • [15] An efficient synthesis of 5-substituted 1H-tetrazoles catalyzed by graphene
    Gang Qi
    Wenguo Zhang
    Yong Dai
    Research on Chemical Intermediates, 2015, 41 : 1149 - 1155
  • [16] Mesoporous ZnS nanospheres: a high activity heterogeneous catalyst for synthesis of 5-substituted 1H-tetrazoles from nitriles and sodium azide
    Lang, Leiming
    Li, Baojun
    Liu, Wei
    Jiang, Li
    Xu, Zheng
    Yin, Gui
    CHEMICAL COMMUNICATIONS, 2010, 46 (03) : 448 - 450
  • [17] Synthesis of 5-substituted 1H-tetrazoles Using Natural and Reusable Natrolite Zeolite
    Sajadi, S. Mohammad
    Maham, Mehdi
    LETTERS IN ORGANIC CHEMISTRY, 2014, 11 (01) : 35 - 39
  • [18] Ammonium acetate mediated synthesis of 5-substituted 1H-tetrazoles
    Dipak R. Patil
    Mukesh B. Deshmukh
    Dipak S. Dalal
    Journal of the Iranian Chemical Society, 2012, 9 : 799 - 803
  • [19] Alkylation of 5-substituted 1H-tetrazoles using the Mitsunobu reaction
    Kumar, Sunil
    Coca, Adiel
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [20] Antimony Trioxide as an Efficient Lewis Acid Catalyst for the Synthesis of 5-Substituted 1H-Tetrazoles
    Venkateshwarlu, G.
    Rajanna, K. C.
    Saiprakash, P. K.
    SYNTHETIC COMMUNICATIONS, 2009, 39 (03) : 426 - 432
12345