AI Article Synopsis
- A novel Smiles-type radical rearrangement technique was created that uses visible light to enable decarboxylation of specific compounds called ω-aryl- N-(acyloxy)phthalimides.
- This method allows for the efficient production of important drug-related substances, including phenylethylamine derivatives, dihydroisoquinolinones, and benzoazepinones, from common starting materials like benzoic acids or benzaldehydes.
- Notably, this approach supports the synthesis of pure D-amphetamine and essential precursors for capsazepinoid bronchodilators, enhancing pharmaceutical development.
Article Abstract
A Smiles-type radical rearrangement induced by visible-light-mediated decarboxylation of ω-aryl- N-(acyloxy)phthalimides was developed, giving rise to pharmacologically important substance classes: phenylethylamine derivatives, dihydroisoquinolinones, and benzoazepinones were synthesized on the basis of readily available benzoic acids or benzaldehydes and β- or γ-amino acids. This methodology facilitates the synthesis of enantiopure D-amphetamine and of precursors of capsazepinoid bronchodilators.
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| http://dx.doi.org/10.1021/acs.joc.8b01538 | DOI Listing |
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