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

Photochemical transformations of small molecules, such as -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...

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Published inOrganic & biomolecular chemistry Vol. 22; no. 38; pp. 7848 - 7853
Main Authors Zhigileva, Ekaterina A, Opryshko, Victoria E, Eshtukov-Shcheglov, Artur V, Ivanov, Dmitrii S, Rudik, Daniil I, Mikhaylov, Andrey A, Ivanov, Igor A, Smirnov, Alexander Yu, Baranov, Mikhail S
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 02.10.2024
Subjects
Acetic acid
Chemical synthesis
Dimethyl sulfoxide
Esters
Irradiation
Photochemicals
Photochemistry
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Summary:Photochemical transformations of small molecules, such as -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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ISSN:1477-0520
1477-0539
1477-0539
DOI:10.1039/d4ob01194e