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

被引：92

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

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2011年 / 9卷 / 06期

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

页码：1938 / 1947

页数：10

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 [J].

Baumann, Marcus ;

Baxendale, Ian R. ;

Ley, Steven V. ;

Smith, Christoper D. ;

Tranmer, Geoffrey K. .

ORGANIC LETTERS, 2006, 8 (23) :5231-5234

[3] A Bifurcated Pathway to Thiazoles and Imidazoles Using a Modular Flow Microreactor [J].

Baxendale, Ian R. ;

Ley, Steven V. ;

Smith, Christopher D. ;

Tamborini, Lucia ;

Voica, Ana-Florina .

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 [J].

Baxendale, Ian R. ;

Deeley, Jon ;

Griffiths-Jones, Charlotte M. ;

Ley, Steven V. ;

Saaby, Steen ;

Tranmer, Geoffrey K. .

CHEMICAL COMMUNICATIONS, 2006, (24) :2566-2568

[5] Preparation of the neolignan natural product grossamide by a continuous-flow process [J].

Baxendale, IR ;

Griffiths-Jones, CM ;

Ley, SV ;

Tranmer, GK .

SYNLETT, 2006, (03) :427-430

[6] Triazolylbenzimidazolthiones and derivatives of the new 1,2,3-triazolo[1,5-a][1,3,5]benzotriazepine heterocycle [J].

Biagi, G ;

Giorgi, I ;

Livi, O ;

Nardi, A ;

Scartoni, V .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2002, 39 (06) :1293-1298

[7] Organic azides:: An exploding diversity of a unique class of compounds [J].

Bräse, S ;

Gil, C ;

Knepper, K ;

Zimmermann, V .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) :5188-5240

[8] ReactIR Flow Cell: A New Analytical Tool for Continuous Flow Chemical Processing [J].

Carter, Catherine F. ;

Lange, Heiko ;

Ley, Steven V. ;

Baxendale, Ian R. ;

Wittkamp, Brian ;

Goode, Jon G. ;

Gaunt, Nigel L. .

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 [J].

Carter, Catherine F. ;

Baxendale, Ian R. ;

O'Brien, Matthew ;

Pavey, John B. J. ;

Ley, Steven V. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (22) :4594-4597

[10]

DASETTIMO A, 1979, FARMACO-ED SCI, V34, P371

← 1 2 3 4 →