Experimental and theoretical study of reactivity and biological activity of stereodefined thiazolidines and their synthetic analogues

Our research covers several areas of organic chemistry with particular interests directed towards study of heterocyclic push-pull molecules with interesting reactivity and structural properties. These compounds of general formula D-pi-A, exhibiting strong D-A interactions via C=C bond (or pi–conjugating spacer) have been studied due to their optoelectronic features. Our approach based on modern theoretical and experimental methods is envisioned in terms of (i) organic synthesis of an extensive series of 5-substituted and 5-unsubstituted 4-oxothiazolidines 1, bearing the trisubstituted exocyclic C=C double bond at the position C-2, (ii) structure elucidation, encompassing also (iii) the dynamics of chemoselective reactions of selected precursors 1. Our group will be involved in further design, synthesis and characterization of new heterocyclic systems derived from substrates 1, with an aim to obtain compounds with promising biological properties. Within the realm of organometallic chemistry a range of transition metal carbonyl anions will be used in reactions with 2-(1-bromoalkylidene)thiazolidin-4-ones as model compounds to compare the rates of the fast halogen-metal exchange and deprotonation in these polyfunctional molecule, containing an acidic lactam hydrogen. Referred as halophilic reactions and to date relatively undeveloped, they occur not at the carbon atom (nucleophilic substitutions), but at the halogen atom with the expulsion of a carbanion as a leaving group.