Copper‐Assisted Synthesis of Novel Pyrazolo[3,4‐d]thiazoles

Based on both the chemical and the biological importance of the pyrazole and the thiazole backbones, we report herein a convenient design of new pyrazolo[3,4‐d]thiazoles for the development of molecules with a high therapeutic potential. The effective and appropriate strategy chosen consists of an i...

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Bibliographic Details
Published in:ChemCatChem 2019-08, Vol.11 (15), p.3530-3533
Main Authors: Ostache, Nicu‐Cosmin, Hiebel, Marie‐Aude, Fînaru, Adriana‐Luminiţa, Guillaumet, Gérald, Suzenet, Franck
Format: Article
Language:English
Subjects:
copper
Liebeskind-Srogl cross-coupling
pyrazole
thiazole
Ullmann cyclisation
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Summary:Based on both the chemical and the biological importance of the pyrazole and the thiazole backbones, we report herein a convenient design of new pyrazolo[3,4‐d]thiazoles for the development of molecules with a high therapeutic potential. The effective and appropriate strategy chosen consists of an intramolecular copper‐catalysed N‐arylation followed by the Liebeskind‐Srogl cross‐coupling reaction. The efficiency of copper and palladium catalysts for the first step of the synthesis was evaluated. These efforts allowed the synthesis of a variety of modulated heterobicycles. Copper can do it: An efficient one‐pot methodology involving copper‐mediated intramolecular N‐arylation followed by the Liebeskind‐Srogl cross‐coupling reaction led to an original library of bifunctionalized pyrazolo[3,4‐d]thiazoles with good to excellent yields.
ISSN:1867-3880
1867-3899
DOI:10.1002/cctc.201900707