Heterocyclic systems with a quinoline scaffold represent privileged scaffold in medicinal chemistry and drug discovery due to the broad biological activities displayed by these derivatives. Reactivity of C2-quinoline substituted furan, tiophene and pyrrole derivatives in palladium-catalyzed direct C–H arylation were investigated. It has been shown that kinetic data points towards the electrophilic metalation-deprotonation reaction mechanism of the transformation. In collaboration with M. Lautens (University of Toronto, Canada) and F. Glorius (Westfälische Wilhelms-Universität Münster, Germany) research groups the one-pot synthesis of a broad variety of dihydrofuroquinolines, dihydrothienoquinolines, and dihydro-benzoquinolines was developed. The combination of the Rh(I)-catalyzed hydroarylation of vinylpyridines with the Pd(0)/Pd(II)-catalyzed direct C−H arylation in a Multicomponent-Multicatalyst Reaction (MC)2R could be used to develop an efficient and step-economic protocol for the rapid construction of molecular complexity.
Synthesis of 8-heteroaryl nitroxoline analogues via one-pot sequential Pd-catalyzed coupling reactions
Employing Pd-Catalyzed C−H Arylation in Multicomponent-Multicatalyst Reactions (MC)2R: One-Pot Synthesis of Dihydrobenzoquinolines
The Influence of the Quinoline Moiety on Direct Pd-Catalyzed Arylation of Five-Membered Heterocycles
Cathepsin B inhibitors: Further exploration of the nitroxoline core
