Efficient Synthesis, Structure Control and Homogeneous Catalytic Hydrogenation of Novel Arylidene Tetramic Acids.
Advancing the chemical engineering fundamentals
Chemical Reaction Engineering (T2-2P)
Keywords: catalytic, hydrogenation, enantioselective, tetramic
Christos Karaiskos[1]*, Maria Tzika[2], Patrina Paraskevopoulou[3], John Markopoulos[3], Olga – Igglessi Markopoulou[1].
[1] Laboratory of Organic Chemistry, Department of Chemical Engineering, National Technical University of Athens, Greece; [2] Department of Chemistry and Biology, University of Siegen, Germany; [3] Department of Chemistry, University of Athens, Greece.
Abstract
Arylidene tetramic acids form a significant group of biologically important compounds. The activity of arylidene tetramic acids depends on the functional groups attached on the main ring structure. The aromatic system can be stabilized or destabilized, depending on the nature of the groups.
The synthesis of arylidene tetramic acids can be controlled in every detail in order to achieve the desired structure. The synthetic route consists of three stages for the 3-alkoxycarbonyl arylidene tetramic acids, but an extra stage is required to detach the 3-alkoxycarbonyl group.
The enantioselective catalytic hydrogenation of the arylidene tetramic acids leads to structures with modified biological activity, similar to that of statins. The primary structure of the substrate is of high importance, and influences the hydrogenation results. A large number of arylidene tetramic acids, with different functional groups, was subjected to a catalytic hydrogenation process, but only the substrates with certain functional groups and structure gave good results.
The hydrogenation processes were performed at high hydrogen pressure (20-55 bar), using an Autoclaves Engineers’ 300 mL reactor controlled with a CT-1000 Control Tower, while a variety of reaction temperatures was employed. Homogeneous hydrogenation was performed using Ru(II)-(BINAP) complexes.
Presented Tuesday 18, 13:30 to 15:00, in session Chemical Reaction Engineering (T2-2P).
