Issue 2, 2015

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

Abstract

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.

Graphical abstract: 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

Supplementary files

Article information

Article type
Paper
Submitted
15 Sep 2014
Accepted
16 Oct 2014
First published
04 Nov 2014

Org. Biomol. Chem., 2015,13, 409-423

Author version available

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

L. L. Corre, L. Tak-Tak, A. Guillard, G. Prestat, C. Gravier-Pelletier and P. Busca, Org. Biomol. Chem., 2015, 13, 409 DOI: 10.1039/C4OB01951B

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