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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

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journal contribution
posted on 2020-07-06, 04:44 authored by Zifeng 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.

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