Photoenolization-induced oxirane ring opening in 2,5-dimethylbenzoyl oxiranes to form pharmaceutically promising indanone derivatives.
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.
Solomek
Tomás
T
Department of Chemistry, Faculty of Science, Masaryk University, Kamenice 5/A8, 625 00 Brno, Czech Republic.
Stacko
Peter
P
Tazhe Veetil
Aneesh
A
Pospísil
Tomás
T
Klán
Petr
P
D000475:Alkenes / Q000737:chemistry*; D005027:Ethylene Oxide / Q000737:chemistry*; D006878:Hydroxides / Q000737:chemistry; D007189:Indans / Q000737:chemistry*; D007834:Lasers; D008958:Models, Molecular; D008968:Molecular Conformation; D010782:Photolysis; D011789:Quantum Theory
D000475:Alkenes; D006878:Hydroxides; D007189:Indans; C031356:hydroxide ion; C013352:indacrinone; D005027:Ethylene Oxide