An efficient synthesis of 5-substituted 1H-tetrazoles via B(C6F5)3 catalyzed [3+2] cycloaddition of nitriles and sodium azide

Prajapti, Santosh Kumar; Nagarsenkar, Atulya; Babu, Bathini Nagendra

doi:10.1016/j.tetlet.2014.04.089

Cited by 52 publications

(20 citation statements)

References 46 publications

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“…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

Applied Organom Chemis

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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.

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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

Applied Organom Chemis

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“…The combined organic layer was washed with water (8 mL) and concentrated it to give yield the crude white crystalline solid 5-phenyl tetrazole in 80-82% yield. The crude tetrazole was then recrystallized by mixture of solvents (50% ethyl acetate in hexane) and subsequently characterized by 1 H NMR, 13 C NMR, IR.…”

Section: Reusability Of Sio 2 -Mtsa General Procedures Of 5-substitutementioning

confidence: 99%

Silica Supported MTSA Catalyst for the Synthesis of 5-Substituted-1H-tetrazole- A Green Chemistry Approach

2018

Chem Sci Trans

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We have developed simple, cost efficient and environmentally benign protocol for the synthesis of 5-substituted 1H-tetrazole via [2+3] cyclo addition reaction from organic nitrile and sodium azide in refluxing DMF by using heterogeneous catalyst as MTSA (Melamine tri sulphonic acid). The corresponding 5-substituted 1H-tetrazole were obtained in lower yield but when using silica supported MTSA the yield obtained 85% in 6 h. After completion of the reaction, the catalyst was recovered by filtration and reused with only a slight decrease of activity observed under the same reaction conditions. Various aliphatic and aromatic nitrile converted in corresponding 5-substituted 1H-tetrazole in excellent yield without any contamination.

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“…Tetrazoles as five membered heterocyclic compounds are of interest in pharmaceuticals, in synthetic organic chemistry, in coordination chemistry as a ligand, in catalysis technology, in the photographic industry and in organometallic chemistry . Also, tetrazoles and their derivatives have been reported as analgesic, antiviral, anti‐inflammatory, anti‐proliferative, antibacterial, potential anti HIV drug candidate, antifungal, herbicidal and anticancer agents . Likewise, the C‐C band formation has been employed in the synthesis of advanced materials and natural products, pharmaceuticals, agrochemicals and biologically active compounds as well as in engineering materials has attracted enormous interest .…”

Section: Introductionmentioning

confidence: 99%

A new Pd‐Schiff‐base complex on boehmite nanoparticles: Its application in Suzuki reaction and synthesis of tetrazoles

Jabbari

Tahmasbi

Nikoorazm

et al. 2018

Applied Organom Chemis

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Boehmite nanoparticles are not air or moisture sensitive, therefore have been prepared in water without inert atmosphere using inexpensive materials. Pd-isatin-boehmite was synthesized and used as heterogeneous organometallic catalyst for the synthesis of 5-substituted 1H-tetrazoles and C-C band formation. Pd-isatin-boehmite characterized by XRD, TGA, SEM and ICP-OES techniques. This catalyst was reused for several times without significant loss of its catalytic efficiency or palladium leaching. Heterogeneity of this catalyst has been studied using ICP-OES technique.

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An efficient synthesis of 5-substituted 1H-tetrazoles via B(C6F5)3 catalyzed [3+2] cycloaddition of nitriles and sodium azide

Cited by 52 publications

References 46 publications

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

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

Silica Supported MTSA Catalyst for the Synthesis of 5-Substituted-1H-tetrazole- A Green Chemistry Approach

A new Pd‐Schiff‐base complex on boehmite nanoparticles: Its application in Suzuki reaction and synthesis of tetrazoles

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An efficient synthesis of 5-substituted 1H-tetrazoles via B(C6F5)3 catalyzed [3+2] cycloaddition of nitriles and sodium azide

Cited by 52 publications

References 46 publications

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

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

Silica Supported MTSA Catalyst for the Synthesis of 5-Substituted-1H-tetrazole- A Green Chemistry Approach

A new Pd‐Schiff‐base complex on boehmite nanoparticles: Its application in Suzuki reaction and synthesis of tetrazoles

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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

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