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Synthesis of (2-Aminophenyl)(naphthalen-2-yl)methanones via Intramolecular Rearrangement of (E)-3-Styrylquinolin-4(1H)-ones under Irradiation with 365 nm UV Light

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A highly efficient and environmentally friendly synthesis of (2-aminophenyl)(naphthalen-2-yl)methanones was developed. The (2-aminophenyl)(naphthalen-2-yl)methanone derivatives were obtained in high yields (up to 96%) by the irradiation of ( E )-3-styrylquinolin-4(1 H… Click to show full abstract

A highly efficient and environmentally friendly synthesis of (2-aminophenyl)(naphthalen-2-yl)methanones was developed. The (2-aminophenyl)(naphthalen-2-yl)methanone derivatives were obtained in high yields (up to 96%) by the irradiation of ( E )-3-styrylquinolin-4(1 H )-ones in EtOH–H 2 O (7:1) with UV light (365 nm) at room temperature under Ar atmosphere. The demonstrated photoinduced intramolecular rearrangement has advantages over other transition-metal-catalyzed reactions, e.g. no requirement of additives, green solvent, broad substrate scope, and high atom efficiency.

Keywords: naphthalen methanones; synthesis aminophenyl; styrylquinolin ones; intramolecular rearrangement; aminophenyl naphthalen

Journal Title: Synlett
Year Published: 2018

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