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 language | English |
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Pages (from-to) | 7848-7853 |
Number of pages | 6 |
Journal | Organic and Biomolecular Chemistry |
Volume | 22 |
Issue number | 38 |
DOIs | |
Publication status | Published - 29 Aug 2024 |
Externally published | Yes |
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