Journal
ORGANIC LETTERS
Volume 19, Issue 21, Pages 5760-5763Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b02690
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- Ludwig-Maximilians-University Munich
- DIP (German-Israeli Project Cooperation)
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A regioselective zincation of the 2-pyridone and 2,7-naphthyridone scaffolds has been developed. Zincations of the methoxyethoxymethyl (MEM)-protected compounds using TMP2Zn.2MgCl(2).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 iPrMgCl.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.
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