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Synthesis of 2‑Substituted Quinolines from 2‑Aminostyryl Ketones Using Iodide as a Catalyst

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journal contribution
posted on 17.04.2018, 00:00 by So Young Lee, Jiye Jeon, Cheol-Hong Cheon
A new protocol for the synthesis of 2-substituted quinolines from 2-aminostyryl ketones has been developed using iodide as a nucleophilic catalyst. Conjugate addition of iodide to 2-aminostyryl ketones yielded the corresponding β-iodoketones, which could have a conformation where the amino and carbonyl groups are proximal through free rotation about the Cα–Cβ single bond. Subsequent condensation between the amino and carbonyl groups followed by elimination of hydrogen iodide provided the corresponding quinolines, with regeneration of the iodide catalyst.