A fully automated, multistep flow synthesis of 5-amino-4-cyano-1,2,3-triazoles

被引:93
作者
Smith, Catherine J. [1 ]
Nikbin, Nikzad [1 ]
Ley, Steven V. [1 ]
Lange, Heiko [1 ]
Baxendale, Ian R. [1 ]
机构
[1] Univ Cambridge, Dept Chem, Innovat Technol Ctr, Cambridge CB2 1EW, England
基金
英国工程与自然科学研究理事会; 美国安德鲁·梅隆基金会;
关键词
CHEMISTRY; MICROREACTORS; REARRANGEMENT; DERIVATIVES; POTENT; AZIDES; BATCH;
D O I
10.1039/c0ob00815j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Having demonstrated in the preceding publication the flow synthesis of aryl azides, we describe here a general protocol for the in-line purification of these versatile intermediates. As part of this investigation, we evaluated the use of ReactIR 45m as a tool for real-time detection of hazardous azide contaminants. This azide synthesis and purification process was then incorporated into a multistep flow sequence to generate a small collection of 5-amino-4-cyano-1,2,3-triazoles directly from aniline starting materials in a fully automated fashion.
引用
收藏
页码:1938 / 1947
页数:10
相关论文
共 33 条
  • [1] BAUMANN M, 2011, MOL DIVERS, DOI DOI 10.3987/COM-10-S(E)77
  • [2] Fully automated continuous flow synthesis of 4,5-disubstituted oxazoles
    Baumann, Marcus
    Baxendale, Ian R.
    Ley, Steven V.
    Smith, Christoper D.
    Tranmer, Geoffrey K.
    [J]. ORGANIC LETTERS, 2006, 8 (23) : 5231 - 5234
  • [3] A Bifurcated Pathway to Thiazoles and Imidazoles Using a Modular Flow Microreactor
    Baxendale, Ian R.
    Ley, Steven V.
    Smith, Christopher D.
    Tamborini, Lucia
    Voica, Ana-Florina
    [J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2008, 10 (06): : 851 - 857
  • [4] A flow process for the multi-step synthesis of the alkaloid natural product oxomaritidine: a new paradigm for molecular assembly
    Baxendale, Ian R.
    Deeley, Jon
    Griffiths-Jones, Charlotte M.
    Ley, Steven V.
    Saaby, Steen
    Tranmer, Geoffrey K.
    [J]. CHEMICAL COMMUNICATIONS, 2006, (24) : 2566 - 2568
  • [5] Preparation of the neolignan natural product grossamide by a continuous-flow process
    Baxendale, IR
    Griffiths-Jones, CM
    Ley, SV
    Tranmer, GK
    [J]. SYNLETT, 2006, (03) : 427 - 430
  • [6] Triazolylbenzimidazolthiones and derivatives of the new 1,2,3-triazolo[1,5-a][1,3,5]benzotriazepine heterocycle
    Biagi, G
    Giorgi, I
    Livi, O
    Nardi, A
    Scartoni, V
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2002, 39 (06) : 1293 - 1298
  • [7] Organic azides:: An exploding diversity of a unique class of compounds
    Bräse, S
    Gil, C
    Knepper, K
    Zimmermann, V
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) : 5188 - 5240
  • [8] ReactIR Flow Cell: A New Analytical Tool for Continuous Flow Chemical Processing
    Carter, Catherine F.
    Lange, Heiko
    Ley, Steven V.
    Baxendale, Ian R.
    Wittkamp, Brian
    Goode, Jon G.
    Gaunt, Nigel L.
    [J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2010, 14 (02) : 393 - 404
  • [9] Synthesis of acetal protected building blocks using flow chemistry with flow IR analysis: preparation of butane-2,3-diacetal tartrates
    Carter, Catherine F.
    Baxendale, Ian R.
    O'Brien, Matthew
    Pavey, John B. J.
    Ley, Steven V.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (22) : 4594 - 4597
  • [10] DASETTIMO A, 1979, FARMACO-ED SCI, V34, P371