Parallel synthesis of 1,2,4-triazole derivatives using microwave and continuous-flow techniques

An efficient and convenient solution-phase synthesis of a 1 H -1,2,4-triazole library with potential agrochemical activity is reported employing microwave-assisted organic synthesis (MAOS) and continuous-flow microfluidic synthetic methods starting from commercially available 3,5-dibromo-1 H -1,2,4-...

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Bibliographic Details
Published in:Molecular diversity 2012-02, Vol.16 (1), p.81-90
Main Authors: Szommer, Tamás, Lukács, András, Kovács, József, Szabó, Miklós J., Hoffmann, Michael G., Schmitt, Monika H., Gerencsér, János
Format: Article
Language:English
Subjects:
Amines - chemistry
Biochemistry
Biomedical and Life Sciences
Bromides - chemistry
Combinatorial Chemistry Techniques - methods
Full-Length Paper
Life Sciences
Magnetic Resonance Spectroscopy
Microfluidics - methods
Microwaves
Molecular Weight
Organic Chemistry
Pharmacy
Polymer Sciences
Rheology
Solvents - chemistry
Triazoles - chemical synthesis
Triazoles - chemistry
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Summary:An efficient and convenient solution-phase synthesis of a 1 H -1,2,4-triazole library with potential agrochemical activity is reported employing microwave-assisted organic synthesis (MAOS) and continuous-flow microfluidic synthetic methods starting from commercially available 3,5-dibromo-1 H -1,2,4-triazole ( 1 ). MAOS was used for the synthesis of 5-amino-3-bromo-1,2,4-triazole analogs 3 and for their 3-aryl derivatives 4 via Suzuki–Miyaura coupling with polymer-supported catalyst. A microfluidic hydrogenation reactor integrated into an automated parallel synthesis platform was built and utilized for the reductive dehalogenation reactions providing 5-aminotriazoles ( 5 ). Graphical Abstract
ISSN:1381-1991
1573-501X
DOI:10.1007/s11030-012-9357-2