tert-Butyl Bromide-Promoted Intramolecular
Cyclization of 2‑Arylamino Phenyl Ketones and Its Combination
with Cu-Catalyzed C–N Coupling: Synthesis of Acridines at Room
Temperature
posted on 2020-07-06, 04:44authored byZifeng Cao, Yuan Zhu, Xiaoman Li, Yang He, Jinli Zhang, Liang Xu, Yu Wei
Herein,
a facile intramolecular cyclization of 2-arylamino phenyl
ketones is established to supersede the traditional high-temperature,
strongly acidic conditions and achieve 9-substituted acridines, by
virtue of the combination of 2,2,2-trifluoroethanol and tert-butyl bromide. This protocol can be merged well with the preceding
Cu-catalyzed intermolecular Chan–Evans–Lam cross-coupling
reactions, therefore enabling pot-economic modular synthesis of 9-substituted
acridines from readily available 2-amino phenyl ketones and aryl boronic
acids at room temperature.