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
Institute of Bioorganic Chemistry Russian Academy of Sciences, Miklukho-Maklaya 16/10, 117997, Moscow, Russia.
Pirogov Russian National Research Medical University, Ostrovitianov 1, 117997, Moscow, Russia.
Org Biomol Chem. 2024 Oct 2;22(38):7848-7853. doi: 10.1039/d4ob01194e.
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.
在没有光催化剂的情况下，小分子（如α-取代苯甲醛）的光化学转化研究得非常少，可能会揭示出意想不到的结果。在本文中，我们表明2-(2-甲酰基苯氧基)乙酸及其酯在365nm光照下会发生光环化反应生成色满酮和苯并呋喃酮衍生物。该反应仅在二甲基亚砜中发生，可用于高效地以良好产率（27-91%）获得羟基色满酮。详细的机理研究揭示了产生各种不同光转化产物的线索。
