Photoinduced Hydrogen Atom Transfer in 2-Formylbenzamides: Amide–Aldehyde 1,2-Transposition and Antioxidant Activity of Isobenzofuranones

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2026-10-19 DOI:10.1021/acs.orglett.6c04158

Svetlana A. Krasnova,Yulia A. Bogdanova,Andrey A. Mikhaylov,Alexander Yu. Smirnov,Mikhail S. Baranov,Dmitrii S. Ivanov

引用次数: 0

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.

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光诱导2-甲酰基苯酰胺中的氢原子转移：酰胺醛1,2-转位和异苯并呋喃酮的抗氧化活性

报道了以2-甲酰基苯酰胺为原料，光诱导分子内1,5-氢原子转移，在无光催化条件下合成异苯并呋喃-1(3H)- 1。在365 nm的醋酸乙酯中辐照得到15个产物，收率为66%-99%。该产物可实现正式的酰胺醛1,2-转位，而选定的衍生物具有清除DPPH自由基和细胞内抗氧化活性。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.