Hydrogen bond assisted ortho-selective C(sp)-H amination of nitrosoarenes and subsequent α-C(sp)-H functionalization of aliphatic amines is achieved under metal-free conditions. The annulation of nitrosoarenes and 2-hydroxy-C-nitroso compounds with N-heterocycles provides a facile excess to a wide range of biologically relevant ring-fused benzimidazoles and structurally novel polycyclic imidazoles, respectively. Nucleophilic aromatic hydrogen substitution (SArH) was found to be preferred over classical SAr reaction during the C(sp)-H amination of halogenated nitrosoarenes.
Unlike other alkylamines, benzylamines upon reaction with a nitrosoarene undergo oxidation to the corresponding imines. A direct amination of benzylamines, which was difficult to achieve due to its facile oxidation, to the corresponding hydrazones is reported. A wide variety of benzylamines and N-heterocycles were reacted with nitrosoarenes to provide structurally diverse hydrazones and hydrazides, respectively. Moreover, the direct N-amination reaction was applied to the one-pot synthesis of triazoles.
Lewis acid catalyzed annulation reaction via arene functionalization of nitrosoarenes, and C-C cleavage of (epoxy)styrene to provide arylquinolines is reported. The Lewis acid catalyst altered the annulation pattern providing arylquinolines...
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