Microwave-assisted preparation of 4-amino-3-cyano-5-methoxycarbonyl-N-arylpyrazoles as building blocks for the diversity-oriented synthesis of pyrazole-based polycyclic scaffolds

The synthesis of 4-amino-3-cyano-N-arylpyrazoles A based on a Thorpe-Ziegler cyclization as the key step has been achieved using microwave activation. Via a new diversity-oriented synthetic pathway, these highly functionalized building blocks allowed the access to various heteroaromatic scaffolds su...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2015-01, Vol.13 (2), p.409-423
Main Authors: Le Corre, Laurent, Tak-Tak, Lotfi, Guillard, Arthur, Prestat, Guillaume, Gravier-Pelletier, Christine, Busca, Patricia
Format: Article
Language:English
Subjects:
Magnetic Resonance Spectroscopy
Microwaves
Pyrazoles - chemical synthesis
Pyrazoles - chemistry
Spectrometry, Mass, Electrospray Ionization
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Summary:The synthesis of 4-amino-3-cyano-N-arylpyrazoles A based on a Thorpe-Ziegler cyclization as the key step has been achieved using microwave activation. Via a new diversity-oriented synthetic pathway, these highly functionalized building blocks allowed the access to various heteroaromatic scaffolds such as pyrazolo-pyridines B, pyrazolo-pyrimidines C and pyrazolo-oxadiazoles D. Interestingly, these platforms contain three to four reactive sites that could be used for post-functionalization in order to further increase the molecular diversity.
ISSN:1477-0520
1477-0539
DOI:10.1039/c4ob01951b