AgNO3 catalyzed synthesis of 5-substituted-1H-tetrazole via [3+2] cycloaddition of nitriles and sodium azide

Boehmite nanoparticles are aluminium oxide hydroxide (γ-AlOOH) particles, which were prepared using a simple and inexpensive procedure in water at room temperature and further modified using arginine. Subsequently palladium particles were immobilized on their surface to prepare Pd-Arg@boehmite. This novel nanostructured compound was fully characterized using thermogravimetric analysis, X-ray diffraction, inductively coupled plasma optical emission (ICP-OES) and energy-dispersive X-ray spectroscopies, and scanning and transmission electron microscopies. Finally, this catalyst was applied as a moisture-and air-stable heterogeneous material for the synthesis of 5-substituted 1H-tetrazole derivatives. The leaching of palladium and heterogeneity of the catalyst were studied using hot filtration and ICP-OES. This catalyst demonstrated remarkable recyclability. The novelty of this work is that it represents the first time an amino acid has been grafted on boehmite nanoparticles.

Section: Introductionmentioning

confidence: 99%

First report of the direct supporting of palladium–arginine complex on boehmite nanoparticles and application in the synthesis of 5‐substituted tetrazoles

Tahmasbi

Ghorbani‐Choghamarani

2016

“…In the last few years, several procedures have been used in the synthesis of these materials including various catalysts such as [HgCl(pzta)] n , ammonium chloride and ammonium fluoride, (NH 4 ) 2 Ce(NO 3 ) 6 , AgNO 3 , Fe 3 O 4 @SiO 2 /Salen Cu(II), ionic liquids, CuO, and CoL 2 , CuL 2 , ZnL 2 and PdL 2 Schiff base complexes . However, most of them have some drawbacks such as toxicity, instability, expensiveness, require the use of high temperature and long reaction times, and difficulty in synthetic procedure.…”

Section: Introductionmentioning

confidence: 99%

Anchoring of Cu(II)–vanillin Schiff base complex on MCM‐41: A highly efficient and recyclable catalyst for synthesis of sulfides and 5‐substituted 1H–tetrazoles and oxidation of sulfides to sulfoxides

Khanmoradi

Nikoorazm

Ghorbani‐Choghamarani

2017

A copper(II)-vanillin complex was immobilized onto MCM-41 nanostructure and was used as an inexpensive, non-toxic and heterogeneous catalyst in the synthesis of symmetric aryl sulfides by the cross-coupling of aromatic halides with S 8 as an effective sulfur source, in the oxidation of sulfides to sulfoxides using 30% H 2 O 2 as a green oxidant and in the synthesis of 5-substituted 1H-tetrazoles from a smooth (3 + 2) cycloaddition of organic nitriles with sodium azide (NaN 3 ). The products were obtained in good to excellent yields. This catalyst could be reused several times without loss of activity. Characterization of the catalyst was performed using Fourier transform infrared, energy-dispersive X-ray and atomic absorption spectroscopies, X-ray diffraction, thermogravimetric analysis, and scanning and transmission electron microscopies.

“…Many methods for the synthesis of 5‐substituted tetrazoles have been proposed based on [3 + 2] cycloaddition of azide ion to corresponding organic nitriles. The reactions were carried out using numerous homogeneous catalysts such as Zn(OTf) 2 , Cu 2 (OTf) 2 , Fe(OAc) 2 , BF 3 –OEt 2 , AlCl 3 and AgNO 3 , and using some heterogeneous catalysts such as Zn/Al hydrotalcite, COY zeolites, γ‐Fe 2 O 3 , nano‐ZnO/Co 3 O 4 , nano‐CuFe 2 O 4 , AlPO‐5 microporous molecular sieves and Fe 3 O 4 @SiO 2 /Salen of Cu(II) …”

Section: Introductionmentioning

confidence: 99%

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

Esmaeilpour

Javidi

Zahmatkesh

2016

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 Fe 3 O 4 @SiO 2 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-Fe 3 O 4 as the core, tetraethoxysilane as the silica source and poly(vinyl alcohol) as the surfactant, and then Fe 3 O 4 @SiO 2 was coated with 1,4-dihydroxyanthraquinonecopper(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.