Photoenolization-induced oxirane ring opening in 2,5-dimethylbenzoyl oxiranes to form pharmaceutically promising indanone derivatives |
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Authors: | Solomek Tomás Stacko Peter Tazhe Veetil Aneesh Pospísil Tomás Klán Petr |
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Institution: | Department of Chemistry, Faculty of Science, Masaryk University, Kamenice 5/A8, 625 00 Brno, Czech Republic. |
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Abstract: | 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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