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

被引：162
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 68 条
  • [1] Fast microwave-assisted preparation of aryl and vinyl nitriles and the corresponding tetrazoles from organo-halides
    Alterman, M
    Hallberg, A
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (23) : 7984 - 7989
  • [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] PREPARATION AND REACTIONS OF 5-VINYLTETRAZOLE
    ARNOLD, C
    THATCHER, DN
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (04) : 1141 - &
  • [4] Aureggi V., 2007, ANGEW CHEM, V119, P8592
  • [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] Aminolysis of Epoxides in a Microreactor System: A Continuous Flow Approach to β-Amino Alcohols
    Bedore, Matthew W.
    Zaborenko, Nikolay
    Jensen, Klavs F.
    Jamison, Timothy F.
    [J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2010, 14 (02) : 432 - 440
  • [7] BERNSTEIN PR, 1987, SYNTHESIS-STUTTGART, P1133
  • [8] Microwave-assisted synthesis of sterically hindered 3-(5-tetrazolyl)pyridines
    Bliznets, IV
    Vasil'ev, AA
    Shorshnev, SV
    Stepanov, AE
    Lukyanov, SM
    [J]. TETRAHEDRON LETTERS, 2004, 45 (12) : 2571 - 2573
  • [9] The Use of Copper Flow Reactor Technology for the Continuous Synthesis of 1,4-Disubstituted 1,2,3-Triazoles
    Bogdan, Andrew R.
    Sach, Neal W.
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (06) : 849 - 854
  • [10] 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
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