Doped Nano‐Sized Copper(I) Oxide (Cu₂O) on MelamineFormaldehyde Resin: a Highly Efficient Heterogeneous Nano Catalyst for ‘Click’ Synthesis of Some Novel 1H‐1,2,3‐Triazole Derivatives Having Antibacterial Activity

Abstract

A facile and simple protocol for the 1,3‐dipolar cycloaddition of organic azides with terminal alkynes catalyzed by doped nano‐sized Cu2O on melamineformaldehyde resin (nano‐Cu2OMFR) as a new and convenient heterogeneous catalyst is described. In this method, ‘click’ cycloaddition of various structurally diverse β‐azido alcohols and alkynes in the presence of nano‐Cu2OMFR in H2O/THF 1 : 2 furnished the corresponding 1,4‐disubstituted 1H‐1,2,3‐triazole adducts 1a–1o in good to excellent yields at room temperature (Scheme and Table 3). The nano‐Cu2OMFR was characterized by scanning electron microscopy (SEM), X‐ray diffraction (XRD), inductively coupled plasma (ICP) analysis, and FT‐IR. The nano‐Cu2OMFR could be easily recovered and recycled from the reaction mixture and reused for many consecutive trials without significant decrease in activity (Table 4). The in vitro antibacterial activities of all synthesized compounds were tested on several Gram‐positive and/or Gram‐negative bacteria (Table 5). The results demonstrate the promising antibacterial activity for some of the synthesized compounds.

Nanoporous Poly(Melamine Formaldehyde) Networks by Aqueous Dispersion Polycondensation—Synthesis and Adsorption Properties

“…Hence, MF, doped with e.g. copper(I) oxide, can be a convenient heterogeneous catalyst . Highly porous MF resins have also been suggested for adsorption of pollutants but do also have very interesting CO 2 adsorption properties .…”

Polymer immobilized Cu(I) formation and azide-alkyne cycloaddition: A one potreaction

“…Applying Cu 2 O powder directly in a title reaction usually results an incomplete conversion and also require long reaction time 16 . Efforts have also been made to enhance the catalytic efficiency of Cu 2 O 17 18 19 20 . It is reported that 17 polyvinylpyrrolidone-coated Cu 2 O nanoparticles can act as an efficient catalyst for cycloaddition reactions in water at physiological temperature.…”

Synthesis of heterocycles and fused heterocycles catalyzed by nanomaterials

“…12), with a diameter of approximately 25 nm and evaluated its catalytic activity in the copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction (Scheme 17, Table 17, Method A). 51 Nano copper-doped silica cuprous sulfate (CDSCS), proved also to be a highly efficient heterogeneous catalyst for the regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles derivatives 41g and 41ah-bj. 50 Rad et al reported that the 1,3-dipolar cycloaddition of organic azides with terminal alkynes 35 can be catalyzed by doped nano-sized Cu 2 O on melamine formaldehyde resin (nano-Cu 2 O MFR) to furnish the corresponding 1,4-disubstituted 1H-1,2,3-triazole adducts 41s-ag in good to excellent yields at room temperature (Scheme 17, Table 17, Method B).…”