Microwave activation in tetrazole chemistry

Мызников, Л. В.; Ворона, Светлана В.; Artamonova, T. V.; Zevatskii, Yu. É.

doi:10.1007/s10593-017-1981-4

Cited by 6 publications

(2 citation statements)

References 62 publications

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“…Reactions of azide ions with organic nitriles usually require polar aprotic solvents (DMF and dimethyl sulfoxide) and prolonged heating at elevated temperatures (70–160 °C). The reaction rates can be increased with the use of catalysts, most typically Zn 2+ or Al 3+ salts and/or microwave irradiation. , Metal-mediated cycloadditions are also known, and these are usually carried out in one of two ways: either with free azides to coordinated nitriles or with metal complexes that include azides with uncomplexed nitriles. Some metal-mediated syntheses rapidly generate coordinated tetrazoles at room temperature; furthermore, cycloaddition reactions of azide ions to highly reactive alkylnitrilium salts have been reported, and some of these reactions even form tetrazoles at room temperature …”

Section: Results and Discussionmentioning

confidence: 99%

Tetrazole Ring Substitution at Carbon and Boron Sites of the Cobalt Bis(dicarbollide) Ion Available via Dipolar Cycloadditions

et al. 2020

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Herein, we describe the synthesis of two families of compounds accessible from [3 + 2] cycloaddition reactions of known B8-substituted isonitrilium and new C1-alkylnitrile and C(1,1′)-dialkylnitrile derivatives of the [(1,2-C 2 B 9 H 11 ) 2 -3,3′-Co-(III)] − ion with an azide ion that produce a tetrazole ring substitution at the cobaltacarborane cage. In addition, we outline the important differences in reactivity observed for the two types [B-isonitrilium/C-(alkyl)nitrile] of cobaltacarborane derivatives. The first family of compounds described corresponds to C5-atomboronated tetrazole rings, with the five-membered moiety in the second type being doubly substituted at the N1 and C5 positions. This substitution opens cobaltacarborane chemistry to a new type of functional group at the cage of potential utility as structural blocks for use in medicinal chemistry or materials science. Our study includes single-crystal X-ray structures of the starting nitriles and both families of tetrazole derivatives, and the structural features that arise from the substitutions are discussed.

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Section: Results and Discussionmentioning

confidence: 99%

Tetrazole Ring Substitution at Carbon and Boron Sites of the Cobalt Bis(dicarbollide) Ion Available via Dipolar Cycloadditions

et al. 2020

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“…Although, reviews published regarding the synthesis and functionalization of tetrazoles, especially for greener synthesis [17] . L. V. Myznikov and group in 2016, provided the comparative details for conventional and microwave‐assisted synthesis of tetrazoles [17a] . A discussion on reports appeared for microwave‐assisted chemical transformations afterwards are collated in this section.…”

Section: Microwave‐assisted Chemistry Of Poly‐aza‐heterocyclesmentioning

confidence: 99%

The Riveting Chemistry of Poly‐aza‐heterocycles Employing Microwave Technique: A Decade Review

et al. 2021

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The application of microwave technique in chemical laboratory rooted back in 1986 and found advantageous over conventional approaches. On the other side, poly‐aza‐heterocycles are influencing organic frameworks with a fascinating chemistry and well explored by employing microwave‐assisted organic reactions. In the present review, we have thoroughly updated rousing literatures of microwave‐assisted synthesis and reactions of various poly‐aza‐heterocycles viz., triazole, tetrazole, triazine, and tetrazine from the past decade (2010–2020). The expedient chemistry and enabling role of microwave heating for adequate chemical transformations of such heterocycles, which were more challenging using classical approaches, are appropriately elucidated. This review also highlights the potential applications of these heterocyclic scaffolds and their derivatives in different scientific domains. Remarkably, such chemical architects possess wide applications as crucial building blocks in synthesis of biologically relevant compounds, agrochemicals, and compounds of interest in material science.

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Cobalt-promoted one-pot reaction of isothiocyanates toward the synthesis of aryl/alkylcyanamides and substituted tetrazoles

Seelam¹,

Kammela²,

Shaikh³

et al. 2018

Chem Heterocycl Comp

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Microwave activation in tetrazole chemistry

Cited by 6 publications

References 62 publications

Tetrazole Ring Substitution at Carbon and Boron Sites of the Cobalt Bis(dicarbollide) Ion Available via Dipolar Cycloadditions

Tetrazole Ring Substitution at Carbon and Boron Sites of the Cobalt Bis(dicarbollide) Ion Available via Dipolar Cycloadditions

The Riveting Chemistry of Poly‐aza‐heterocycles Employing Microwave Technique: A Decade Review

Cobalt-promoted one-pot reaction of isothiocyanates toward the synthesis of aryl/alkylcyanamides and substituted tetrazoles

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