OXIDATION OF THIOPHENE GROUP IN TIOCONAZOLE TO TIOCONAZOLE S-OXIDE USING m-CPBA*AND ENANTIOSEPARATION OF RESULTING COMPOUND VIA HPLC METHOD

Author: Natia Inadze
Keywords: thiophene group oxidation, tioconazole sulfoxide, enantioseparation
Annotation:

Thiophene S-oxides are considerably important organic compounds, especially in medical chemistry and drug metabolism analysis due to their ability to function as key intermediates for synthesis of corresponding thiophenes in biological metabolic pathways in living organisms.1The purpose of this study was to synthesize thiophene S-oxides from tioconazole, a synthetic derivative of imidazole, which inhibits the cell-wall synthesis of fungi. The target compound was thought to have somewhat similar biological activity, including reactions with membrane receptors, transporters and other enzymes.2 At first, for thiophene group oxidation in the sample compound, 77% m-CPBA was used as an oxidizing agent. In order to have avoided the synthesis of thiophene dioxides and have ensured non-complete oxidation, molar ratio of 1:1 of tioconazole to m-CPBA was mixed. The reaction was carried out at 0oC, in an ice-bath. Thin-layer chromatography with two kinds of moving phases (9 CH2Cl2:1 CH3OH and 1 C6H14:1 AcOEt) was utilized for the purpose of observing reaction progress. Then, the resulting racemate was run under HPLC for separating the presumably synthesized enantiomers. As a result of the investigation, it was found that the thiophene group was oxidized under introduced conditions and tioconazole S-oxide was synthesized. The resulting compound was investigated using IR and NMR spectroscopies. The detection and resolution of the two enantiomers of tioconazole sulfoxide were possible via High Performance Liquid Chromatography Method.