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Mannich Reaction of Secondary Amines, Aldehydes and Alkynes in Water Using Cu/C Nanoparticles as a Heterogeneous Catalyst

H. Sharghi^a,*, R. Khalifeh^a,b, F. Moeini^a, M.H. Beyzavi^a, A. Salimi Beni^c and M.M. Doroodmand^a

^aDepartment of Chemistry, Shiraz University, Shiraz, 71454, Iran
^bDepartment of Chemistry, Shiraz Uuniversity of Technology, Shiraz 75555-313, Iran
^cDepartment of Chemistry, Yasouj University, Yasouj, 75918-74831, Iran

The use of 2 mol% of Cu/C nanoparticles, as an easily accessible and inexpensive heterogeneous catalyst, promoted a one-pot three-component condensation of an amine, aldehyde, and an alkyne in water to produce the corresponding propargylamine in good to high yields. This method was proved to be applicable to a wide range of substrates and is especially practical for the synthesis of new azacrown ether derivatives. The catalyst was quantitatively recovered from the reaction by a simple filtration and reused for at least ten times with almost consistent activity.

Keywords: Mannich reaction, Cu/C nanoparticles, Heterogeneous catalyst, Water, Azacrown ether and anthraquinone derivatives