Multicomponent Synthesis of Heterocycles Catalysed by Copper Nanoparticles

MARÍA JOSE ALBALADEJO; FRANCISCO ALONSO; YANINA MOGLIE

Budapest

Conferencia; 20th International Conference on Organic Synthesis; 2014

Universidad de Budapest

In the last few years, we have been interested in the application of supported copper nanoparticles to multicomponent reactions, such as the A3 coupling or the click synthesis of 1,2,3-triazoles from different azido precursors in water. More recently, a one-pot protocol for the synthesis of 1,2,3-triazoles has been developed starting from inactivated alkenes and based on two click reactions: the azidosulfenylation of the carbon-carbon double bond and the copper-catalysed azide-alkyne cycloaddition.High yields of the b-methylsulfanyl triazoles have been attained using CuNPs/C as catalyst, with other commercial copper catalysts being completely inactive. The versatility of the CuNPs/C catalyst allowed the multicomponent synthesis of indolizines(from pyridine-2-carbaldehyde derivatives, secondary amines, and terminal alkynes) in dichloromethane and the synthesis of heterocyclic chalcones under solvent-free conditions. The reactivity of the aforementioned indolizines has also been studied.