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Synthesis 2024; 56(03): 496-506
DOI: 10.1055/a-2183-0262
DOI: 10.1055/a-2183-0262
paper
Photo-Induced Electrophilic Aromatic Substitution of Ferric Acyl Nitrene
Financial support from the Natural Science Foundation of Zhejiang Province (LY22B020010) is gratefully acknowledged.
Abstract
A photo-induced intramolecular electrophilic aromatic substitution (SEAr) 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 SEAr 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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2183-0262.
- Supporting Information
- CIF File
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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