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References (33)
-
(2011)
15:2382–2391.Mak XY, Laurino P, Seeberger PH -
A. Herath, N. Cosford (2010)
One-step continuous flow synthesis of highly substituted pyrrole-3-carboxylic acid derivatives via in situ hydrolysis of tert-butyl esters.Organic letters, 12 22
-
I. Dzvinchuk, T. Makitruk, M. Lozinskii (2003)
2-Acylmethyl-1H-benzimidazoles in the Biginelli ReactionChemistry of Heterocyclic Compounds, 39
-
T. Glasnov, D. Vugts, Manoe Koningstein, Bimbisar Desai, Walter M. F. Fabian, R. Orru, C. Kappe (2006)
Microwave-assisted Dimroth Rearrangement of Thiazines to Dihydropyrimidinethiones: Synthetic and Mechanistic AspectsQsar & Combinatorial Science, 25
-
E. García‐Egido, Stephanie Wong, B. Warrington (2002)
A Hantzsch synthesis of 2-aminothiazoles performed in a heated microreactor system.Lab on a chip, 2 1
-
T Razzaq, C O Kappe (2010)
20411525Chem. Asian J., 5
-
(2001)
For microwave assisted Biginelli reactions, see: Stadler A, Kappe CO -
J. Metzger (1984)
4.19 – Thiazoles and their Benzo Derivatives, 4
-
A. Hantzsch, J. Weber (1887)
Ueber Verbindungen des Thiazols (Pyridins der Thiophenreihe)European Journal of Inorganic Chemistry, 20
-
C. Kappe (2000)
Biologically active dihydropyrimidones of the Biginelli-type--a literature survey.European journal of medicinal chemistry, 35 12
-
Xiao Mak, P. Laurino, P. Seeberger (2009)
Asymmetric reactions in continuous flowBeilstein Journal of Organic Chemistry, 5
-
L. Kürti, B. Czako, E. Corey, K. Nicolaou (2005)
Strategic applications of named reactions in organic synthesis: background and detailed mechanisms -
T. Mayer, T. Kapoor, S. Haggarty, R. King, S. Schreiber, T. Mitchison (1999)
Small molecule inhibitor of mitotic spindle bipolarity identified in a phenotype-based screen.Science, 286 5441
-
T. Wirth (2008)
Microreactors in organic synthesis and catalysis -
All microfluidic syntheses were conducted on a Syrris AFRICA synthesis station using Syrris etched glass chips -
D. Grant, R. Dahl, N. Cosford (2008)
Rapid multistep synthesis of 1,2,4-oxadiazoles in a single continuous microreactor sequence.The Journal of organic chemistry, 73 18
-
W. Ehrfeld, V. Hessel, H. Löwe (2000)
Microreactors: New Technology for Modern Chemistry -
D. Huryn, N. Cosford (2007)
Chapter 26 The Molecular Libraries Screening Center Network (MLSCN): Identifying Chemical Probes of Biological SystemsAnnual Reports in Medicinal Chemistry, 42
-
Lifeng Kang, B. Chung, R. Langer, A. Khademhosseini (2008)
Microfluidics for drug discovery and development: from target selection to product lifecycle management.Drug discovery today, 13 1-2
-
P Biginelli (1891)
10.1002/cber.189102402126Ber, 24
-
Juliya Kharchenko, O. Detistov, V. Orlov (2009)
Synthesis of substituted 5-(1,2,4-oxadiazol-5-yl)-3,4-dihydropyrimidine-2(1H)-thiones.Journal of combinatorial chemistry, 11 2
-
I. Baxendale, S. Ley, Christopher Smith, L. Tamborini, Ana-Florina Voica (2008)
A bifurcated pathway to thiazoles and imidazoles using a modular flow microreactor.Journal of combinatorial chemistry, 10 6
-
(2004)
For recent selected reviews -
Damien Webb, T. Jamison (2010)
Continuous flow multi-step organic synthesisChemical Science, 1
-
I. Baxendale, J. Hayward, S. Ley (2007)
Microwave reactions under continuous flow conditions.Combinatorial chemistry & high throughput screening, 10 10
-
Alexander Stadler, C. Kappe (2001)
Automated library generation using sequential microwave-assisted chemistry. Application toward the Biginelli multicomponent condensation.Journal of combinatorial chemistry, 3 6
-
T. Glasnov, C. Kappe (2011)
Continuous-flow syntheses of heterocyclesJournal of Heterocyclic Chemistry, 48
-
I. Dzvinchuk, T. Makitruk, M. Lozinskii (2002)
2-Phenacylbenzothiazole in the Biginelli ReactionChemistry of Heterocyclic Compounds, 38
-
N. Cosford, L. Tehrani, J. Roppe, E. Schweiger, N. Smith, Jeffrey Anderson, L. Bristow, J. Brodkin, Xiaohui Jiang, I. McDonald, Sara Rao, M. Washburn, M. Varney (2003)
3-[(2-Methyl-1,3-thiazol-4-yl)ethynyl]-pyridine: a potent and highly selective metabotropic glutamate subtype 5 receptor antagonist with anxiolytic activity.Journal of medicinal chemistry, 46 2
-
(2007)
Drug Discov Today -
It should be noted that no improvement in yield was observed with addition of 1 equiv water to the α-bromoketone stock solution. Thus, water was not incorporated into the two-chip sequences -
A. Herath, R. Dahl, N. Cosford (2010)
Fully automated continuous flow synthesis of highly functionalized imidazo[1,2-a] heterocycles.Organic letters, 12 3
-
A. Chighine, G. Sechi, M. Bradley (2007)
Tools for efficient high-throughput synthesis.Drug discovery today, 12 11-12
- Publisher
- Springer Journals
- Copyright
- Copyright © Akadémiai Kiadó 2011
- ISSN
- 2062-249X
- eISSN
- 2063-0212
- DOI
- 10.1556/jfchem.2011.00001
- Publisher site
- See Article on Publisher Site
Abstract
The first example of a sequential heterocycle formation/multicomponent reaction using an automated continuous flow microreactor assembly is reported. Consecutive Hantzsch thiazole synthesis, deketalization, and Biginelli multicomponent reaction provides rapid and efficient access to highly functionalized, pharmacologically significant 5-(thiazol-2-yl)-3,4-dihydropyrimidin-2(1H)-ones without isolation of intermediates. These complex small molecules are generated in reaction times less than 15 min and in high yields (39–46%) over three continuous chemical steps.
Journal
Journal of Flow Chemistry – Springer Journals
Published: Jan 1, 2011
Keywords: flow chemistry; microreactors; multistep synthesis; Hantzsch thiazole synthesis; hydrobromic acid; Biginelli reaction