Paper
Deoxydative substitution of pyridine 1-oxides by thiols. Part XX. Reactions of (2, 3, and 4-phenyl)-, 3-acetamido-, 3-bromo-, 3-acetoxy-, 3-ethoxypyridine 1-oxides with 1-adamantanethiol in acetic anhydride†
Published Jun 1, 1991 · Supaluk Prachayasittikul, G. Doss, L. Bauer
Journal of Heterocyclic Chemistry
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Abstract
Substitutions of 2, 3, and 4-substituted pyridine 1-oxides by 1-adamantanethiol in acetic anhydride takes place at available α-, to a lesser degree at β-, and rarely at γ-ring carbons. It was found that 2-phenylpyridine 1-oxide produces a mixture of 5- and 6-(1-adamantylthio)-2-phenylpyridines, and 4-phenylpyridine 1-oxide a mixture of 2- and 3-isomeric sulfides. Substitutions of the 1-oxides of 3-phenyl-, 3-acetamido-, 3-acetoxy-, 3-bromo-, and 3-ethoxypyridine by 1-adamantanethiol in acetic anhydride led to mixtures consisting predominantly of 2- and 6-sulfide, and to a lesser extent, the 5-sulfide. When triethylamine is present in otherwise identical reaction mixtures, the ratio of α to β-sulfides increases. From the reactions of 3- and 4-phenylpyridine 1-oxides, there were isolated some N-acetyl hydroxy (or acetoxy) 1-adamantylthio substituted 1,2,3,4-and 1,2,3,6-tetrahydropyridines, whose structures are discussed.
Substitution of 2, 3, and 4-substituted pyridine 1-oxides by 1-adamantanethiol in acetic anhydride produces mixtures of 2- and 6-sulfide compounds, with triethylamine increasing the ratio of to -sulfides
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