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

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*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish
Pages (from-to)7848-7853
Number of pages6
JournalOrganic and Biomolecular Chemistry
Volume22
Issue number38
DOIs
Publication statusPublished - 29 Aug 2024
Externally publishedYes

Funding

The authors gratefully acknowledge support from the Russian Science Foundation, grant no. 20-73-10195.

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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