Issue 18, 2023

Immobilization of Ni(ii) complex on the surface of mesoporous modified-KIT-6 as a new, reusable and highly efficient nanocatalyst for the synthesis of tetrazole and pyranopyrazole derivatives

Abstract

In this paper, KIT-6@SMTU@Ni was successfully synthesized via a new method of Ni(II) complex stabilization on modified mesoporous KIT-6, as a novel and green heterogeneous catalyst. The obtained catalyst (KIT-6@SMTU@Ni) was characterized using Fourier transform infrared spectroscopy (FT-IR), Brunauer–Emmett–Teller (BET) calculation, X-ray diffraction (XRD), atomic absorption spectroscopy (AAS), energy-dispersive X-ray spectroscopy (EDS), X-ray mapping, thermogravimetric analysis (TGA) techniques and scanning electron microscopy (SEM). After complete characterization of the catalyst, it was successfully used for the synthesis of 5-substituted 1H-tetrazoles and pyranopyrazoles. Moreover, tetrazoles were synthesized from benzonitrile derivatives and sodium azide (NaN3). All tetrazole products were synthesized with high TON, TOF and excellent yields (88–98%) in a reasonable time (0.13–8 h), demonstrating the efficiency and practicality of the KIT-6@SMTU@Ni catalyst. Furthermore, pyranopyrazoles were prepared through the condensation reaction of benzaldehyde derivatives with malononitrile, hydrazine hydrate and ethyl acetoacetate with high TON, TOF and excellent yields (87–98%) at appropriate times (2–10.5 h). KIT-6@SMTU@Ni could be reused for five runs without any re-activation. Significantly, this plotted protocol has prominent benefits, such as applying green solvents, the use of commercially available and low-cost materials, excellent separation and reusability of the catalyst, short reaction time, high yield of products and a facile work-up.

Graphical abstract: Immobilization of Ni(ii) complex on the surface of mesoporous modified-KIT-6 as a new, reusable and highly efficient nanocatalyst for the synthesis of tetrazole and pyranopyrazole derivatives

Supplementary files

Article information

Article type
Paper
Submitted
27 12 2022
Accepted
07 4 2023
First published
24 4 2023
This article is Open Access
Creative Commons BY license

RSC Adv., 2023,13, 12572-12588

Immobilization of Ni(II) complex on the surface of mesoporous modified-KIT-6 as a new, reusable and highly efficient nanocatalyst for the synthesis of tetrazole and pyranopyrazole derivatives

M. Darabi, M. Nikoorazm, B. Tahmasbi and A. Ghorbani-Choghamarani, RSC Adv., 2023, 13, 12572 DOI: 10.1039/D2RA08269A

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