facile, highly efficient and novel method for synthesis of 5-substituted 1H-tetrazoles catalysed by copper(I) chloride

Esirden, İbrahim; Başar, Erhan; Kaya, Muharrem

doi:10.1515/chempap-2015-0124

Cited by 10 publications

(4 citation statements)

References 42 publications

(31 reference statements)

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“…Most of them are based on the addition of the nitrile group of the trimethylsilyl azide (TMSN 3 ) and the sodium azide (NaN 3 ). [16][17][18][19][20][21] Also, different new pathways have been improved, [22][23][24][25][26] such as the catalytic method using a stoichiometric amount of inorganic salts [27][28][29][30][31][32] and metal complex, 33 also using TMSN 3 and TBAF instead of metal salts under solvent-free conditions 17 or in micellar media 34 and ionic liquid. 35 However, these homogeneous catalysts pose difficulties in reusability, recovery and separation.…”

Section: Introductionmentioning

confidence: 99%

A rapid and novel method for the synthesis of 5-substituted 1H-tetrazole catalyzed by exceptional reusable monodisperse Pt NPs@AC under the microwave irradiation

et al. 2015

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A series of 5-substituted 1H-tetrazoles were synthesized in DMF by the [3+2] cycloaddition reaction under the effect of microwave irradiation (10-30 min., fixed mode, 90 o C, 140 W) in the presence of highly efficient superior catalyst. For this reaction, different aromatic nitriles with the sodium azide were used and superior monodisperse (Md) platinum nanoparticles (Pt NPs) decorated on activated carbon (AC) served as a catalyst. Md-Pt NPs@AC were reproducibly and easily produced by double solvent reduction of PtCl4 in room temperature and characterized by transmission electron microscopy (TEM), the high resolution electron micrograph (HRTEM), X-ray diffraction (XRD), atomic force microscopy (AFM) and X-ray photoelectron spectroscopy (XPS). The sum of their results shows the formation of highly crystalline and colloidally stable Md-Pt NPs@AC. The catalytic performance of these new NPs were investigated for the synthesis of 5substituted 1H-tetrazoles, in which they were found to be exceptional reusable, isolable, stable and highly efficient heterogeneous catalyst. All prepared tetrazole products were obtained with perfect yield by using current heterogeneous catalyst and characterized by melting points, FT-IR, 1 H-NMR, 13 C-NMR and HRMS analyzes. RSC Advances

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Section: Introductionmentioning

confidence: 99%

A rapid and novel method for the synthesis of 5-substituted 1H-tetrazole catalyzed by exceptional reusable monodisperse Pt NPs@AC under the microwave irradiation

et al. 2015

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“…During this reaction, silver azide is generated in‐situ and acts as a catalytic species. In another studies, Copper (I) chloride was used to get 5‐substituted‐1H‐tetrazole derivatives 47%–90% (Scheme 1; Esirden et al, 2015). In this study, researchers compared the effect of CuCl 2 with CuI, CuSO 4 , ZnCl 2 , AlCl 3 as catalyst and found that CuCl 2 were much effective and produced higher yield in short time.…”

Section: Conventional Approachmentioning

confidence: 99%

Tetrazole: A privileged scaffold for the discovery of anticancer agents

et al. 2022

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Carcinoma, characterized by abnormal growth of cells and tissue, is a ubiquitously leading cause of mortality across the globe due to some carcinogenic factors. Currently, several anticancer agents are commercially available in the global market. However, due to their resistance and cost, researchers are gaining more interest in developing newer novel potential anticancer agents. In the search for new drugs for clinical use, the tetrazole ring system has emerged as an exciting prospect in the optimization studies of promising lead molecules. Among the various heterocyclic agents, tetrazole-containing compounds have shown significant promise in the treatment of a wide range of diseases, particularly cancer. Here, in this review, we focused on several synthetic approaches for the synthesis of tetrazole analogs, their targets for treating cancer along with the biological activity of some of the recently reported tetrazole-containing anticancer agents.

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“…Although this procedure was simple enough, but using homogenous Zn (II) salts brought its own problem in separating of heavy metal at the end of the reaction, especially in industrial scale. In recent years, many homo‐ and heterogeneous catalysts have been used for this purpose such as silica sulfuric acid, Mw−Pd/Co@CNT NPs, Fe 3 O 4 @SiO 2 ‐TCT‐PVA−Cu(II), Pt‐NPs@VC, Zn hydroxyapatite, Zn/Al hydrotalcite, Cu 2 O, diisopropylethylammonium acetate, Fe(OAc) 2 , CdCl 2 , SiO 2 ‐H 3 BO 3 , Cu–MCM‐41, Pd‐SBT@MCM‐41, CuO nanoparticles, copper (I) chloride, [Cu(phen)(PPh 3 ) 2 ]NO 3 and so on . Although in many of these reported catalysts, the desired products were formed, but a number of them have some drawbacks such as prolonged reaction time, moderate yield, homogeneous or non‐scalable catalyst and problem in their reusability.…”

Section: Introductionmentioning

confidence: 99%

Preparation of 5‐Substituted‐1H‐Tetrazoles Catalyzed by MOFs via Two Strategies: Direct Condensation of Aryl Nitriles with Sodium Azide, and Tri‐Component Reaction Method

2018

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Various 5‐substituted‐1H‐tetrazoles were synthesized via two strategies; direct [3+2] cycloaddition of substituted aryl nitriles with sodium azide, and tri‐component reaction of aldehydes, hydroxylamine hydrochloride with sodium azide in dimethylformamide (DMF) by applying M2(BDC)2(DABCO) [M: Cu, Co and Ni, BDC=1, 4‐benzenedicarboxylic acid, and DABCO= 1,4‐diazabicyclo[2.2.2]octane] as heterogeneous catalyst. Short reaction time, high yield, totally straightforward procedure and easy work‐up, as well as preparing tetrazole derivatives via relatively cheap and easily available aldehydes (in three‐component method) are some beneficial features of mentioned methodologies. It was found that among three studied transition metals, copper has a unique advantage over other metals in formation of the desired product.

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facile, highly efficient and novel method for synthesis of 5-substituted 1H-tetrazoles catalysed by copper(I) chloride

Cited by 10 publications

References 42 publications

A rapid and novel method for the synthesis of 5-substituted 1H-tetrazole catalyzed by exceptional reusable monodisperse Pt NPs@AC under the microwave irradiation

A rapid and novel method for the synthesis of 5-substituted 1H-tetrazole catalyzed by exceptional reusable monodisperse Pt NPs@AC under the microwave irradiation

Tetrazole: A privileged scaffold for the discovery of anticancer agents

Preparation of 5‐Substituted‐1H‐Tetrazoles Catalyzed by MOFs via Two Strategies: Direct Condensation of Aryl Nitriles with Sodium Azide, and Tri‐Component Reaction Method

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