Abstract
AbstractQuinoline 1‐oxides 1 readily react with 3‐arylrhodanines 2 in the presence of acetic anhydride to afford 3‐aryl‐5‐(2‐quinolyl)rhodanines 3 in high yields. These products resist hydrolysis under both alkaline and acidic conditions, but is oxidized to quinaldinic acid 1‐oxide 4 with 30% hydrogen peroxide in hot acetic acid. Besides isoquinoline 2‐oxide 5, pyridine 1‐oxide 7a also reacts in the same way to give 3‐aryl‐5‐(2‐pyridyl)rhodanines 8, although the reactivity of γ‐picoline 1‐oxide 7b is considerably lower. Contrary to 3, 3‐phenyl‐5‐(2‐pyridyl)rhodanine 8a is successfully hydrolyzed with boiling 48% hydrobromic acid to 2‐pyridinemethanethiol 10 in 57% yield.
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