Reactions of substituted pyridines and their N-oxides with ethanolic sodium hydroxide and various alkoxides

2-Benzoylpyridine 1-oxide with ethanoiic sodium hydroxide yielded acyl nucleophilic displacement products and a redox product, 2-(α-hydroxybenzyl)pyridine. 3-Benzoylpyridine 1-oxide under the same conditions yielded only a reduction product, 3-(α-hydroxybenzyl)-pyridine 1-oxide, whereas 4-benzoylpyridine 1-oxide yielded only a redox product, 4-(α-hydroxy-benzyl)pyridine. The redox reaction which is promoted by base occurs with an α-hydroxybenzylpyridine 1-oxide which results from a carbonyl reduction of the starting material. The benzoyl-pyridine 1-oxides reacted qualitatively the same with sodium ethoxide or isopropoxide as they did with ethanoiic sodium hydroxide, but they reacted differently with potassium t-butoxide or aluminum isopropoxide. The cyano- and benzenesulfonyl-pyridine 1-oxides reacted with ethanolic sodium hydroxide to yield pyridinecarboxylic acids and 1-hydroxypyridones, respectively.