Ring Transformation of Heterocycles by Oxidizing Agents. A ¹⁴C-Study of the Conversion of Quinolines into Indoles by Hydrogen Peroxide

Abstract

Based on experiments with 8-nitro-[2, 4-¹⁴C]-quinoline and 8-nitro-[4-¹⁴C]-quinoline, it has been found that during the ring transformation of 8-nitroquinoline into 7-nitrooxindole by action of hydrogen peroxide in acetic acid, the C₂-atom of the quinoline ring is expelled. A mechanism for the ring transformation is proposed.