Directed Zincation or Magnesiation of the 2-Pyridone and 2,7-Naphthyridone Scaffold Using TMP Bases

Autor: Ziegler, Dorothée S., Greiner, Robert, Lumpe, Henning, Kqiku, Laura, Karaghiosoff, Konstantin, Knochel, Paul
Zdroj: Organic Letters; 20240101, Issue: Preprints
Abstrakt: A regioselective zincation of the 2-pyridone and 2,7-naphthyridone scaffolds has been developed. Zincations of the methoxyethoxymethyl (MEM)-protected compounds using TMP2Zn·2MgCl2·2LiCl (TMP = 2,2,6,6-tetramethylpiperidyl) followed by trapping with electrophiles provided functionalized 2-pyridones and 2,7-naphthyridones. I/Mg exchange of iodinated 2-pyridone and 2,7-naphthyridone using i-PrMgCl·LiCl afforded magnesiated intermediates that reacted with electrophiles. A second magnesiation of the 2-pyridone scaffold was achieved by using TMPMgCl·LiCl. Additionally, we report CoCl2-catalyzed cross-couplings of the 1-chloro-2,7-naphthyridines with arylzinc halides.
Databáze: Supplemental Index