2-(2-formylphenyloxy)acetic acid 衍生物的光化学：羟基色满酮和苯并呋喃酮的合成。

IF 2.9 3区化学 Q1 CHEMISTRY, ORGANIC

Organic & Biomolecular Chemistry Pub Date : 2024-09-04 DOI:10.1039/d4ob01194e

Ekaterina A Zhigileva, Victoria E Opryshko, Artur V Eshtukov-Shcheglov, Dmitrii S Ivanov, Daniil I Rudik, Andrey A Mikhaylov, Igor A Ivanov, Alexander Yu Smirnov, Mikhail S Baranov

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引用次数: 0

摘要

在没有光催化剂的情况下，小分子（如正交取代的苯甲醛）的光化学转化研究明显不足，可能会出现意想不到的结果。在本文中，我们发现 2-(2-甲酰基苯氧基)乙酸及其酯类在 365 纳米波长的照射下会发生光环化反应，生成色满酮和苯并呋喃酮衍生物。该反应只在二甲基亚砜中发生，可用于高效地获得羟基色满酮，收率高达 27-91%。详细的机理研究揭示了多种产物发生不同光转化的线索。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Photochemistry of 2-(2-formylphenyloxy)acetic acid derivatives: synthesis of hydroxychromanones and benzofuranones.

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Photochemistry of 2-(2-formylphenyloxy)acetic acid derivatives: synthesis of hydroxychromanones and benzofuranones.

Photochemical transformations of small molecules, such as ortho-substituted benzaldehydes, in the absence of a photocatalyst are significantly underexplored and may reveal unexpected outcomes. In the present paper, we showed that 2-(2-formylphenoxy)acetic acid and its esters undergo photocyclization into chromanone and benzofuranone derivatives under 365 nm irradiation. The reaction occurs exclusively in dimethyl sulfoxide and can be used to efficiently obtain hydroxychromanones in good yields (27-91%). A detailed mechanistic study revealed the clue of the divergent phototransformation with various products.

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来源期刊

Organic & Biomolecular Chemistry 化学-有机化学

CiteScore

5.50

自引率

9.40%

发文量

1056

审稿时长

1.3 months

期刊介绍： The international home of synthetic, physical and biomolecular organic chemistry.