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o-Nitrobenzyl Oxime Ethers Enable Photoinduced Cyclization Reaction to Provide Phenanthridines under Aqueous Conditions.

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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… Click to show full abstract

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.

Keywords: reaction; nitrobenzyl oxime; photoinduced cyclization; aqueous conditions; cyclization; oxime ethers

Journal Title: Organic letters
Year Published: 2023

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