β-Cyclodextrin-mediated highly efficient [2+3] cycloaddition reactions for the synthesis of 5-substituted 1H-tetrazoles

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

“…Tetrazoles and their derivatives have been reported as anti‐viral, anti‐bacterial, anti‐inflammatory and herbicidal agents, potential anti‐HIV drug candidates and anti‐proliferative, analgesic and anti‐tumour agents . Tetrazoles can be used as isosteric replacements for carboxylic acids in drug design and have found use in information recording systems …”

Section: Introductionmentioning

confidence: 99%

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

Moradi

Ghorbani‐Choghamarani

2016

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.

“…The resulting product, although evident as a single compound by TLC, was purified by simple recrystallization from aqueous ethanol giving pure tetrazoles 3 a‐af . Products for 3 a to 3 r reported . All products were pure enough for IR and NMR spectroscopic analyses.…”

Section: Methodsmentioning

confidence: 99%

“…Earlier repоrted methods for the synthesis of 5‐sustituted 1 H ‐tetrazole suffered from drаwbacks such as the use of strong Lewis acids or expensive and toxic metals. In order to overcome these difficulties, severаl new mild methods recently described, among them the use of TMSN 3 –TBAF, FeCl 3 – SiO 2, Zn/Al‐hydrocаlcite, Fe 2 O 3, Zn hydroxyapatite, Sb 2 O 3, NaHSO 4 .SiO 2 or I 2, mesoporous ZnS nanospheres, tungstаtes as novel heterogeneous catalysts,25a CuFe 2 O 4 25b and β‐Cyclodextrin . However, some of these methоds still require long reaction times to achieve reasonable yields, environmentally hazardous catalysts, and tedious purification of the products.…”

Section: Introductionmentioning

confidence: 99%

Iron (III)‐porphyrin Complex FeTSPP as an efficient catalyst for synthesis of tetrazole derivatives via [2 + 3]cycloaddition reaction in aqueous medium

El‐Remaily

Elhady

2019

The metal complex (5,10,15,20-tetrakis-(4-sulfonatophenyl)-porphyrin-iron (III) chloride (FeTSPP) was new employed in an environmentally benign protocol as an efficient catalyst for a "click" chemistry approach for the synthesis of tetrazole and guanindinyltetrazole derivatives via [2 + 3] cycloaddition reaction of nitriles and azide derivatives in aqueous medium. The synthesized compounds were obtained in excellent yield, short reaction times and a recoverable catalyst.