Lithiation of 1-methyl-4-quinolone and 1-methylquinoline-4-thione with lithium diisopropylamide (LDA) at –78 °C takes place at C-2. The resulting lithio-species react with a variety of electrophiles to give 2-substituted-4-quinolones and -quinolines-4-thiones respectively. 1-Methylquinoline-4-thione is easily converted into 1-methyl-4-quinolone in protic solution.
M. Alvarez, M. Salas, L. Rigat, A. de Veciana and J. A. Joule, J. Chem. Soc., Perkin Trans. 1, 1992, 351 DOI: 10.1039/P19920000351
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