Photoenolization-induced oxirane ring opening in 2,5-dimethylbenzoyl oxiranes to form pharmaceutically promising indanone derivatives
Language English Country United States Media print
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
20883047
DOI
10.1021/jo101515a
Knihovny.cz E-resources
- MeSH
- Alkenes chemistry MeSH
- Ethylene Oxide chemistry MeSH
- Photolysis * MeSH
- Hydroxides chemistry MeSH
- Indans chemistry MeSH
- Quantum Theory MeSH
- Lasers MeSH
- Molecular Conformation MeSH
- Models, Molecular MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Alkenes MeSH
- Ethylene Oxide MeSH
- hydroxide ion MeSH Browser
- Hydroxides MeSH
- indacrinone MeSH Browser
- Indans MeSH
Irradiation of 2,5-dimethylbenzoyl oxiranes results in a relatively efficient and high-yielding formation of β-hydroxy functionalized indanones that structurally resemble biologically active pterosines. Nanosecond laser flash photolysis and quantum-chemical calculations based on density functional theory provided evidence that this photochemical transformation proceeds primarily via a photoenolization mechanism. Our study revealed considerable complexity of the mechanism and that structural modifications can significantly alter the reaction pathway and yield different products. The scope of this photochemical transformation for the synthesis of some pharmaceutically important compounds was investigated.
References provided by Crossref.org
Photoremovable protecting groups in chemistry and biology: reaction mechanisms and efficacy
The power of solvent in altering the course of photorearrangements
