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

Ziegler, Dorothee S.; Greiner, Robert; Lumpe, Henning; Kqiku, Laura; Karaghiosoff, Konstantin und Knochel, Paul (2017): Directed Zincation or Magnesiation of the 2-Pyridone and 2,7-Naphthyridone Scaffold Using TMP Bases. In: Organic Letters, Bd. 19, Nr. 21: S. 5760-5763

Abstract

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.

• Dokumententyp: Zeitschriftenartikel
• Fakultät: Chemie und Pharmazie > Department Chemie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• ISSN: 1523-7060
• Sprache: Englisch