Ammonium acetate mediated synthesis of 5-substituted 1H-tetrazoles

An efficient and general method is reported for the synthesis of 5-substituted 1Htetrazole derivatives in the presence of S-methylisothiourea complex of palladium immobilized on boehmite nanoparticles (Pd-SMTU@boehmite) as an efficient and recyclable nanocatalyst. Boehmite nanoparticles were not sensitive to air or moisture and were prepared without inert atmosphere in water at room temperature. Then a novel type of phosphine-free palladium complex was immobilized on these nanoparticles. This catalyst was characterized using Fourier transform infrared, thermogravimetric, Brunauer-Emmett-Teller, transmission and scanning electron microscopic, energy-dispersive X-ray spectroscopic, X-ray diffraction and inductively coupled plasma optical emission spectroscopic techniques. The catalyst was reused several times without palladium leaching or change in its structure.

Section: Introductionmentioning

confidence: 99%

Efficient synthesis of 5‐substituted tetrazoles catalysed by palladium–S‐methylisothiourea complex supported on boehmite nanoparticles

Moradi

Ghorbani‐Choghamarani

2016

“…Protonolysis of intermediate II by H + of NH 4 OAc or acidic extraction with HCl affords the 5‐substituted 1 H ‐tetrazole and NiFe 2 O 4 catalyst. Ammonium acetate may produce ammonium azide in situ by reaction of ammonium acetate and sodium azide, increasing the availability of azide ion for [3 + 2] cycloaddition with nitrile, and also ammonium acetate is used as proton source to provide pure tetrazoles …”

Section: Resultsmentioning

confidence: 99%

Synthesis of 5‐substituted 1H‐tetrazoles using a recyclable heterogeneous nanonickel ferrite catalyst

Abrishami

Ebrahimikia

Rafiee

2015

An efficient method was developed for the [2 + 3] cycloaddition of sodium azide with nitriles to afford 5‐substituted 1H‐tetrazoles using nanonickel ferrite (NiFe2O4) as an effective heterogeneous catalyst in dimethylformamide. The main advantages of this method are high yields, simple methodology and easy work‐up. The catalyst can be recovered and reused for several cycles with predictable activity. Copyright © 2015 John Wiley & Sons, Ltd.

“…Tetrazoles as versatile heterocyclic compounds have been considered for various applications including propellants, [ 11 ] explosive materials, [ 12 ] medicinal industry, organic, and organometallic chemistry. [ 13–15 ] Losartan and valsartan, the two famous tetrazole‐based medications are prescribed to control high blood pressure. [ 16 ] Other applications that can be named for tetrazole derivatives are considered as antitumor, antibacterial, herbicidal materials, and antivirus for binding to HIV.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 5‐substituted 1H‐tetrazoles and oxidation of sulfides by using boehmite nanoparticles/nickel‐curcumin as a robust and extremely efficient green nanocatalyst

Jani

Bahrami

2020

Nickel‐anchored curcumin‐functionalized boehmite nanoparticles (BNPs@Cur‐Ni) as a robust and versatile nanocatalyst was synthesized and well‐characterized by using Fourier transform infrared (FT‐IR), transmission electron microscopy (TEM), scanning electron microscopy (SEM), energy dispersive X‐ray (EDX), X‐ray mapping, thermogravimetric analysis (TGA), differential thermal analysis (DTA), Brunauer–Emmett–Teller (BET), X‐ray diffraction (XRD), and inductively coupled plasma optical emission spectroscopy (ICP‐OES). The synthesis of 5‐substituted 1H‐tetrazoles and the oxidation of sulfides were conducted by BNPs@Cur‐Ni with excellent turnover number (TON) and turnover frequency (TOF) outcomes. Also, the catalyst was reused for several sequential runs without Ni leaching or decreasing in reaction yield. Utilizing the curcumin and boehmite with a natural source as well as poly(ethylene glycol) (PEG) as a solvent in this simple protocol can be based on green chemistry rules.