Photo-Induced Electrophilic Aromatic Substitution of Ferric Acyl Nitrene

Abstract

A photo-induced intramolecular electrophilic aromatic substitution (S_EAr) of N-acyloxyamides using FeCl₃ in 1,4-dioxane is reported for the synthesis of biologically interesting benzoxazin-3(4H)-ones. It is believed that irradiation with a blue LED facilitates the reaction, serving as a source of energy. The S_EAr reaction pathway is ascribed to the electronic effects present in the aryl ring of the substrates. The reaction is also applicable for the synthesis of useful scaffolds possessing a quinolin-2-one core, such as an anticancer reagent and analogues of brexipiprazole and cilostamide.

Key words

photo-induced - S_EAr - benzoxazin-3(4H)-ones - iron catalysis - nitrenes

Publication History

Received: 29 August 2023

Accepted after revision: 27 September 2023

Accepted Manuscript online:
27 September 2023

Article published online:
20 November 2023

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