Outline
DOI: 10.1021/acs.orglett.6c04158 ISSN: 1523-7060
Photoinduced Hydrogen Atom Transfer in 2-Formylbenzamides: Amide–Aldehyde 1,2-Transposition and Antioxidant Activity of Isobenzofuranones
Svetlana A. Krasnova, Yulia A. Bogdanova, Andrey A. Mikhaylov, Alexander Yu. Smirnov, Mikhail S. Baranov, Dmitrii S. IvanovAbstract
A photocatalyst-free synthesis of isobenzofuran-1(3H)-ones from 2-formylbenzamides via photoinduced intramolecular 1,5-hydrogen atom transfer is reported. Irradiation at 365 nm in ethyl acetate afforded 15 products in 66%–99% yields. The products enable formal amide–aldehyde 1,2-transposition, while selected derivatives exhibited DPPH radical-scavenging and intracellular antioxidant activities.
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