American Chemical Society
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Synthesis of Polysubstituted Quinolines via Transition-Metal-Free Oxidative Cycloisomerization of o‑Cinnamylanilines

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journal contribution
posted on 2015-04-03, 00:00 authored by Mohammad Rehan, Gurupada Hazra, Prasanta Ghorai
An efficient synthesis of 2-aryl 4-substituted quinolines from stable and readily available o-cinnamylanilines, prepared from anilines and cinnamylalcohols, has been developed. The reaction occurred via a regioselective 6-endo-trig intramolecular oxidative cyclization using KOtBu as a mediator and DMSO as an oxidant at rt. The reaction showed a broad substrate scope with good to excellent yields.