3 years ago

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

Directed Zincation or Magnesiation of the 2-Pyridone and 2,7-Naphthyridone Scaffold Using TMP Bases
Konstantin Karaghiosoff, Paul Knochel, Dorothée S. Ziegler, Laura Kqiku, Henning Lumpe, Robert Greiner
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02690

DOI: 10.1021/acs.orglett.7b02690

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