One pot three-component synthesis of 5-substituted 1 H -tetrazole from aldehyde

Magnetic mesoporous silica nanocomposite, Fe3O4@MCM‐41, was prepared and functionalized with N‐(2‐aminoethyl)‐3‐aminopropyltrimethoxysilane (AEAPS). Then Schiff base grafted nanoparticles were synthesized by the condensation of 5,5'‐methylene bis (salicylaldehyde) and then benzhydrazide with Fe3O4@MCM‐41‐AEAPS. Finally, by adding Cu (CH3COOH)2.H2O, the magnetic nanoparticles (MNPs) functionalized with Cu (II) Schiff base complex were synthesized. The new organic–inorganic hybrid nanocomposite was characterized by FT‐IR, PXRD, AAS, BET, TGA, VSM, FE‐SEM, HRTEM and EDX techniques. Then, the performance of this copper based magnetic nanocatalyst was investigated for the synthesis of 5‐substituted 1H‐tetrazole derivatives using one pot three‐component reactions of various aldehydes, hydroxyl amine hydrochloride and sodium azide. The catalyst can be easily isolated from the reaction mixture by applying an external magnet and reused for at least 5 times without significant loss in catalytic activity. Also, the antibacterial activity of the streptomycin loaded magnetic nanoparticles against Gram‐positive (S. aureus) and Gram‐negative (E. coli) bacteria in the presence and absence of a magnetic field were studied. Results revealed that when these materials exposed to the magnetic field, bacteriostatic activity of nanocomposites was increased. Furthermore, the enzyme immobilization ability of the synthesized compounds was investigated and the results showed that these nanoparticles efficiently immobilized amylase enzyme.

Section: Catalytic Studymentioning

confidence: 99%

Anchoring of Cu (II)‐Schiff base complex on magnetic mesoporous silica nanoparticles: catalytic efficacy in one‐pot synthesis of 5‐substituted‐1H‐tetrazoles, antibacterial activity evaluation and immobilization of α‐amylase

Ahmadi

Sedaghat

Motamedi

et al. 2020

“…A comparison of the catalytic activities of various catalysts for the synthesis of 5‐(4‐methoxyphenyl)‐1 H ‐tetrazole is given in Table . It is clearly axiomatic from the Table that the Pd/MnO 2 nanocomposite outperformed other catalysts that are reported in the literature . The reaction was carried out in the presence of the Pd/MnO 2 nanocomposite in shorter time.…”

Section: Resultsmentioning

confidence: 87%

Biosynthesis of Pd/MnO₂ nanocomposite using Solanum melongena plant extract and its application for the one‐pot synthesis of 5‐substituted 1H‐tetrazoles from aryl halides

Nasrollahzadeh

Ghorbannezhad

Sajadi

2018

In this work, for the first time, Solanum melongena plant extract was used for the green synthesis of Pd/MnO 2 nanocomposite via reduction osf Pd(II) ions to Pd(0) and their immobilization on the surface of manganese dioxide (MnO 2 ) nanoparticles (NPs) as an effective support. The synthesized nanocomposite were characterized by various analytical techniques such as Fourier transform infrared (FT-IR), X-ray diffraction (XRD), transmission electron microscopy (TEM), field emission scanning electron microscopy (FESEM), energy dispersive X-ray spectroscopy (EDS) and UV-Vis spectroscopy. The catalytic activity of Pd/MnO 2 nanocomposite was used as a heterogeneous catalyst for the one-pot synthesis of 5-substituted 1H-tetrazoles from aryl halides containing various electron-donating or electron-withdrawing groups in the presence of K 4 [Fe (CN) 6 ] as non-toxic cyanide source and sodium azide. The products were obtained in good yields via a simple methodology and easy work-up. The nanocatalyst can be recycled and reused several times with no remarkable loss of activity. Highlights:• Green synthesis of Pd/MnO 2 nanocomposite using Solanum melongena extract.• Pd/MnO 2 nanocomposite was characterized by FT-IR, XRD, FESEM, EDS and TEM.• One-pot synthesis of 5-substituted 1H-tetrazoles from aryl halides using Pd/MnO 2 nanocomposite.• The catalyst can be easily recycled and reused several times without sensible loss in its catalytic efficiency.

“…In order to compare the efficiency of [t-Bu 2 Sn(OH) (H 2 O)] 2 2+ 2OTf − with other catalysts reported in the literature for the preparation of 2,4,6-triarylpyridines as well as to exhibit the merit of the present work, our results are compared with those of some other previously reported studies (Table 10). [5] 2 TiCl 3 (20 mol%), DMF, reflux, 4 h 86 [6] 3 Cu(OAc) 2 (20 mol%), choline chloride-urea, 100°C, 12 h 90 [7] 4 PVA@Cu Schiff base complex (0.43 mol%), H 2 O, r.t., 7 min 98 [8]…”

Section: Structure Of Catalystmentioning

confidence: 99%

“…In view of the availability, lower toxicity and ease of handling of aldehydes as compared to nitriles, the application of aldehydes for the synthesis of tetrazole derivatives is a highly attractive and advantageous strategy. From a literature survey, we came to know that only a few processes have been reported for the synthesis of 5‐substituted 1 H ‐tetrazoles from aldehydes and the catalysts used were (NH 4 ) 4 Ce(SO 4 ) 4 ·2H 2 O, TiCl 3 , Cu(OAc) 2 , PVA@Cu Schiff base complex, I 2 , Cu‐MCM‐41, [bmim]N 3 /Cu (OAc) 2 and P 2 O 5 . So, these areas remain largely unexplored.…”

Section: Introductionmentioning

confidence: 99%

Cationic organotin cluster [t‐Bu₂Sn(OH)(H₂O)]₂²⁺2OTf⁻‐catalyzed one‐pot three‐component syntheses of 5‐substituted 1H‐tetrazoles and 2,4,6‐triarylpyridines in water

Wang

Zhao

et al. 2019

The cationic organotin cluster [t‐Bu2Sn(OH)(H2O)]22+2OTf− is easy to prepare and stable in air. The catalytic activity of [t‐Bu2Sn(OH)(H2O)]22+2OTf− as a neutral organotin Lewis acid catalyst is probed through the one‐pot three‐component syntheses of 5‐substituted 1H‐tetrazoles from aldehydes, hydroxylamine hydrochloride and sodium azide, and of 2,4,6‐triarylpyridines from aromatic aldehydes, substituted acetophenones and ammonium acetate. The reactions proceed well in the presence of 1 mol% of [t‐Bu2Sn(OH)(H2O)]22+2OTf− in water and provide the corresponding 5‐substituted 1H‐tetrazoles and 2,4,6‐triarylpyridines in good to excellent yields. The method reported has several advantages such as the catalyst being neutral, low catalyst loading and use of water as a green solvent.