Ring lithiation of pyridones
- 1 January 1988
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 1,p. 1-8
- https://doi.org/10.1039/p19880000001
Abstract
Lithiation of 1-methyl-2-pyridone takes place mainly at the methyl group which then leads to a dimer (11) by addition to a second mol equivalent of pyridone at C-6. Lithiation of 1-methyl-4-pyridone takes place cleanly and efficiently at C-2; this lithio derivative gave a dimer (13) with a second mol equivalent of the pyridone and reacted with a variety of carbon electrophiles to produce 2-substituted 4-pyridones (14c–n). 1-Methoxymethyl-, 1-benzyloxymethyl-, and 1-(2-trimethylsilylethoxy)-methyl-4-pyridones also lithiate at C-2, though these lithio derivatives were much less reactive towards electrophiles.Keywords
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