Grafting Cu(II)-5-amino-1H-tetrazole complex on magnetic graphene oxide as an efficient magnetically recoverable catalyst for the synthesis of N-benzyl-N-aryl-5-amino-1H-tetrazoles

Research output: Contribution to journalResearch articleContributedpeer-review

Contributors

  • Hanieh Gharoubi - , University of Qom (Author)
  • Mahmoud Nasrollahzadeh - , University of Qom (Author)
  • Zahra Khorsandi - , University of Qom (Author)
  • Marcos A.L. Nobre - , Universidade Estadual Paulista Júlio de Mesquita Filho (Author)
  • Sungkyun Choi - , Seoul National University (Author)
  • Benjamin Kruppke - , Chair of Biomaterials (Author)
  • Hossein Ali Khonakdar - , Chair of Biomaterials, Iran Polymer and Petrochemical Institute (Author)

Abstract

In this study, a new approach has been developed for the synthesis of a novel catalyst based on Cu(II)-5-amino-1H-tetrazole complex immobilized on the surface of graphene oxide-modified magnetic nanoparticles (GO/Fe3O4@Tet-Cu(II)) by 3-chloropropyltrimethoxysilane ((MeO)3Si-PrCl) as a linker. The synthesis of GO/Fe3O4@Tet-Cu(II) was confirmed by FT-IR (Fourier transform-infrared spectroscopy), XRD (X-ray diffraction), VSM (Vibrating sample magnetometer), TG-DTG (Thermogravimetry and differential thermogravimetry), EDS (energy dispersive X-ray spectroscopy), elemental mapping, and TEM (transmission electron microscopy). GO/Fe3O4@Tet-Cu(II) showed high catalytic activity in the synthesis of N-benzyl‐N‐aryl‐5‐amino‐1H‐tetrazoles via the reaction of N-benzyl-N-arylcyanamides and NaN3 in DMF solvent at 120 °C in a short reaction time with good yields. The catalyst can be recycled for five runs without losing its efficiency and demonstrates excellent chemical stability and high potential for practical synthetic applications. N-Benzyl‐N‐aryl‐5‐amino‐1H‐tetrazoles were characterized using FT-IR and NMR analyses. The present strategy could help design and synthesize future catalysts for organic synthesis.

Details

Original languageEnglish
Article number110653
Number of pages11
JournalInorganic Chemistry Communications
Volume153
Publication statusPublished - Jul 2023
Peer-reviewedYes

External IDs

WOS 001001468200001
unpaywall 10.1016/j.inoche.2023.110653

Keywords

Keywords

  • Cu(II) complex, Graphene oxide, Heterogeneous catalyst, Magnetic catalyst, N‐Benzyl‐N‐aryl‐5‐amino‐1H‐tetrazoles, N-Benzyl-N-aryl-5-amino-1H-tetrazoles