4.6 Article

Selective and Stepwise Functionalization of the Pyridazine Scaffold by Using Thio-Substituted Pyridazine Building Blocks

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume -, Issue -, Pages -

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202302156

Keywords

cross-coupling; magnesium amides; metalation; N-heterocycles; pyridazine

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A regioselective tri- and tetra-functionalization of the pyridazine scaffold was achieved using two readily available building blocks, resulting in the synthesis of a range of pyridazine derivatives.
We described a regioselective tri- and tetra-functionalization of the pyridazine scaffold using two readily available building blocks: 3-alkylthio-6-chloropyridazine and 3,4-bis(methylthio)-6-chloropyridazine by performing selective metalations with TMPMgCl center dot LiCl and catalyst-tuned cross-coupling reactions with arylzinc halides. Several of the resulting pyridazines were converted into more elaborated N-heterocycles such as thieno[2,3-c]pyridazines and 1H-pyrazolo[3,4-c]pyridazines.

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