A biocompatible chitosan-ionic liquid hybrid catalyst for regioselective synthesis of 1,2,3-triazols

Int J Biol Macromol. 2019 Nov 1:140:939-948. doi: 10.1016/j.ijbiomac.2019.08.162. Epub 2019 Aug 19.

Abstract

A new type of quadruple hybrid system was prepared containing chitosan (CS), folic acid (FA), Poly(styrene-co-maleic anhydride) [SMA] and ionic liquid (IL). This nanocatalyst was synthesized by the functionalization of SMA with folic acid and then polymerization with chitosan in the presence of DCC and NHS. CuI was immobilized onto this support to provide Cu@SMA-FA-CS-IL. The catalyst was fully characterized by using different characterization techniques such as FTIR, 1H NMR, ICP, SEM, EDX, TGA, and XRD. This Cu (I) heterogeneous species was successfully applied in the reaction of sodium azide, terminal alkynes, and alkyl halides or α-haloketones in water to afford 1,4-disubstituted-1,2,3-triazoles within relatively short reaction times. Moreover, the catalyst is recyclable for five reaction cycles with minor CuI leaching and slight drop of the catalytic activity.

Keywords: 1,2,3-Triazoles; Biopolymer; Chitosan; Click reaction; Cu (I) nanoparticles; Ionic liquid; SMA.

MeSH terms

  • Biocompatible Materials / chemistry*
  • Catalysis
  • Chitosan / chemistry*
  • Ionic Liquids / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Nanoparticles / chemistry
  • Spectroscopy, Fourier Transform Infrared
  • Thermogravimetry
  • Triazoles / chemical synthesis*
  • Triazoles / chemistry

Substances

  • Biocompatible Materials
  • Ionic Liquids
  • Triazoles
  • Chitosan