Photoinduced Hydrogen Atom Transfer in 2-Formylbenzamides: Amide–Aldehyde 1,2-Transposition and Antioxidant Activity of Isobenzofuranones
Abstract 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.
Authors
- Mikhail S. Baranov (ORCID: https://orcid.org/0000-0002-9339-7603)
- Dmitrii S. Ivanov (ORCID: https://orcid.org/0009-0003-2434-2806)
- Alexander Yu. Smirnov (ORCID: https://orcid.org/0000-0002-1545-6604)
- Andrey Andreevich Mikhaylov (ORCID: https://orcid.org/0000-0001-9433-9141)
- Svetlana A. Krasnova (ORCID: https://orcid.org/0009-0002-7401-1928)
- Yulia A. Bogdanova (ORCID: https://orcid.org/0000-0003-1745-4204)
Institutions
- Pirogov Russian National Research Medical University (RU)
- Institute of Bioorganic Chemistry (RU)
Publication Details
- Journal
- Organic Letters
- Published
- 2026-10-19
- DOI
- https://doi.org/10.1021/acs.orglett.6c04158
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00