One-pot synthesis of 1- and 5-substituted 1H-tetrazoles using 1,4-dihydroxyanthraquinone-copper(II) supported on superparamagnetic Fe3O4@SiO2 magnetic porous nanospheres as a recyclable catalyst

• Published in: Applied organometallic chemistry Vol. 30; no. 11; pp. 897 - 904
• Main Authors: Esmaeilpour, Mohsen, Javidi, Jaber, Zahmatkesh, Saeed
• Format: Journal Article
• Language: English
• Published: HOBOKEN Blackwell Publishing Ltd 01.11.2016; Wiley
• Subjects: 1- and 5-substituted 1H-tetrazoles; Chemistry; Chemistry, Applied; Chemistry, Inorganic & Nuclear; core-shell; magnetic nanocatalyst; magnetic separation; one-pot reactions; Physical Sciences; Science & Technology; magnetic separation; SODIUM-AZIDE; 3-COMPONENT SYNTHESIS; one-pot reactions; EFFICIENT SYNTHESIS; IONIC LIQUID; REUSABLE HETEROGENEOUS CATALYST; TRIMETHYLSILYL AZIDE; 3+2 CYCLOADDITION; CARBON NANOTUBES; NANOPARTICLES; COUPLING REACTIONS; 1-and 5-substituted 1H-tetrazoles; magnetic nanocatalyst; core-shell
• ISSN: 0268-2605; 1099-0739
• DOI: 10.1002/aoc.3518

An effective one‐pot, convenient process for the synthesis of 1‐ and 5‐substituted 1H‐tetrazoles from nitriles and amines is described using1,4‐dihydroxyanthraquinone–copper(II) supported on Fe3O4@SiO2 magnetic porous nanospheres as a novel recyclable catalyst. The application of this catalyst allows the synthesis of a variety of tetrazoles in good to excellent yields. The preparation of the magnetic nanocatalyst with core–shell structure is presented by using nano‐Fe3O4 as the core, tetraethoxysilane as the silica source and poly(vinyl alcohol) as the surfactant, and then Fe3O4@SiO2 was coated with 1,4‐dihydroxyanthraquinone–copper(II) nanoparticles. The new catalyst was characterized using Fourier transform infrared spectroscopy, X‐ray diffraction, transmission electron microscopy, field emission scanning electron microscopy, dynamic light scattering, thermogravimetric analysis, vibration sample magnetometry, X‐ray photoelectron spectroscopy, nitrogen adsorption–desorption isotherm analysis and inductively coupled plasma analysis. This new procedure offers several advantages such as short reaction times, excellent yields, operational simplicity, practicability and applicability to various substrates and absence of any tedious workup or purification. In addition, the excellent catalytic performance, thermal stability and separation of the catalyst make it a good heterogeneous system and a useful alternative to other heterogeneous catalysts. Also, the catalyst could be magnetically separated and reused six times without significant loss of catalytic activity. Copyright © 2016 John Wiley & Sons, Ltd. Synthesis of 1‐ and 5‐substituted 1H‐tetrazoles using 1,4‐dihydroxyanthraquinone–copper(II) supported on Fe3O4@SiO2 nanospheres