Imidazo[1,2-a]pyridines and especially their amide derivatives exhibit a wide range of favourable pharmacological properties. In this work, Pd-catalysed carbonylation was used for the first time for the introduction of the carboxamide moiety into positions 6 or 8. A recyclable Pd catalyst, with palladium immobilised on a supported ionic liquid phase decorated with pyridinium ions, was used efficiently for the conversion of 6- or 8-iodo derivatives to the products. In the case of 6-iodo derivatives, a competing mono- and double carbonylation could be observed in the reactions of aliphatic amines as nucleophiles, but under the proper choice of reaction conditions, good-to-excellent selectivities could be achieved towards either the corresponding amides or α-ketomides. The heterogeneous catalyst showed excellent recyclability and low Pd-leaching.
The combination of the ferrocene skeleton with pharmacophores often leads to molecules with interesting biological properties. Five ferrocene-benzofuran hybrids of different structures were synthesized by transition metal catalyzed reactions. The efficiency of both homogeneous and heterogeneous catalytic methods was tested. The products were characterized using 1H, 13C NMR and FTIR spectroscopy, HRMS and cyclic voltammetry. The structure of one of the new compounds was also proved with X-ray crystallography. The new hybrids showed moderate cytotoxicity on MCF-7 and MDA-MB-231 cell lines. It is remarkable that the less curable MDA-MB-231 cell line was more sensitive to treatment with three ferrocene derivatives.