https://espci.zoom.us/j/88400420441
Title : Sustainable Metal-catalysed Synthesis of Heterocycles
Maria Manuel B. Marques, NOVA School of Science and Technology, Portugal
Abstract :
Azaindoles are bioisosteres of the indole nucleus, a privileged structure, which have enticed the interest of the scientific
community for their physicochemical and pharmacological properties. Azaindoles are rare in nature and highly interesting
in medicinal chemistry and drug discovery programs. This is mainly due to the fact that its solubility, lipophilicity, target
binding and ADME-tox properties can be modulated and tuned, constituting an enormous advantage over other
heterocyclic compounds.1 However, synthesis of azaindoles is challenging. The electron-deficient nature of the pyridine
ring alters the electronic properties of the conjugated system in such a way that many classic indole synthetic methods
are not as ecient or simply do not work. Due to their important value, we have developed methods for the synthesis of
azaindoles, relying on palladium-catalyzed cross-coupling reactions and developed different practical approaches
compatible with all azaindole isomers.2,3 Our group has been focused on metal-catalyzed cross-coupling reactions for the
straightforward synthesis of azaindoles from commercially available aminopyridines. In particular, we have been
exploring Pd-catalysed one-pot methodologies such as the C-N cross-coupling/Heck reaction4 also with Pdnanocatalysts;
5 the N-arlyation/Sonogashira/cyclization reaction;6 and Pd-catalysed C-N cross-coupling/C-H
functionalization.7 Herein we will present our latest achievements on the one-pot reactions, and simple protocols towards
not easy to make heterocycles.
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