Photoenolization-induced oxirane ring opening in 2,5-dimethylbenzoyl oxiranes to form pharmaceutically promising indanone derivatives
Jazyk angličtina Země Spojené státy americké Médium print
Typ dokumentu časopisecké články, práce podpořená grantem
PubMed
20883047
DOI
10.1021/jo101515a
Knihovny.cz E-zdroje
- MeSH
- alkeny chemie MeSH
- ethylenoxid chemie MeSH
- fotolýza * MeSH
- hydroxidy chemie MeSH
- indany chemie MeSH
- kvantová teorie MeSH
- lasery MeSH
- molekulární konformace MeSH
- molekulární modely MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- alkeny MeSH
- ethylenoxid MeSH
- hydroxide ion MeSH Prohlížeč
- hydroxidy MeSH
- indacrinone MeSH Prohlížeč
- indany 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.
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