o -Nitrobenzyl Oxime Ethers Enable Photoinduced Cyclization Reaction to Provide Phenanthridines under Aqueous Conditions.
Hidenori OkamuraMomoka IidaYui KaneyamaFumi NagatsugiPublished in: Organic letters (2023)
In this paper, we describe a novel N-O photolysis of o -nitrobenzyl oxime ethers that enables the synthesis of phenanthridines via intramolecular cyclization reactions. Without the use of additional photocatalysts or photosensitizers, the process proceeds with an efficiency of ≤96% upon exposure of the sample to near-visible light (405 nm) under aqueous conditions. Through the photoinduced production of a fluorescent phenanthridine derivative in HeLa cells, the progress of the reaction under biological conditions was demonstrated. This photoinduced cyclization reaction could be used as a different photochemical instrument to control biological processes by inducing the production of bioactive molecules.