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Directed Zincation or Magnesiation of the 2-Pyridone and 2,7-Naphthyridone Scaffold Using TMP Bases.
- Source :
-
Organic Letters . 11/3/2017, Vol. 19 Issue 21, p5760-5763. 4p. - Publication Year :
- 2017
-
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•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. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 15237060
- Volume :
- 19
- Issue :
- 21
- Database :
- Academic Search Index
- Journal :
- Organic Letters
- Publication Type :
- Academic Journal
- Accession number :
- 126093312
- Full Text :
- https://doi.org/10.1021/acs.orglett.7b02690