Advances in synthesis of tetrazoles coordinated to metal ions

Popova, E. A.; Trifonov, R. E.; Островский, В. А.

doi:10.3998/ark.5550190.0013.102

Cited by 30 publications

(21 citation statements)

References 37 publications

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“…Much attention has been paid to the study of the physicochemical properties of tetrazoles, mainly for their remarkable reactivity observing many peculiarities of tetrazole system such as its charge distribution over its substituted derivatives that influence the reactions routes. The substitution of carbon or nitrogen atom in the heterocycle was thoroughly studied [8,9] as well as the possibility to build complexes [10,11] and salts with metals [12]. Another goal of researchers has been the study of diazenes containing the tetrazole system.…”

Section: Introductionmentioning

confidence: 99%

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5-(Azulen-1-yldiazenyl)tetrazoles; Syntheses and Properties

Bîrzan¹,

Cristea²,

Tecuceanu³

et al. 2020

Rev. Chim.

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The tetrazole-5-diazonium salt, obtained by diazotizing 5-aminotetrazole in strong acid solution, was coupled with azulenes in the presence of pyridine to produce 5-(azulen-1-yldiazenyl)tetrazoles in good yields. The tetrazole moiety was monoalkylated in 1- and in 2- position using dimethyl sulfate for methylation and benzyl bromide for benzylation. The excess of alkylating agent generated in small amount tetrazole dialkylated salts. The synthesized compounds were characterized and some of their properties have been investigated, such as optical, magnetical and electrical.

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Section: Introductionmentioning

confidence: 99%

“…Salts of azotetrazole dianion with protonated nitrogen bases such as guanidinium are gas generators with the potential use in air bags, systems for extinguishing fire or as an additive in solid rocket propellants [14,15]. Carefully attention has also been given to salts of azotetrazole with metals [5,11,12,[16][17][18].…”

Section: Introductionmentioning

confidence: 99%

5-(Azulen-1-yldiazenyl)tetrazoles; Syntheses and Properties

Bîrzan¹,

Cristea²,

Tecuceanu³

et al. 2020

Rev. Chim.

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“…Tetrazoles exhibit excellent coordination abilities through their four nitrogen atoms, acting either as multidentate ligands or as bridging building blocks in supramolecular assemblies [1][2][3][4]. Additionally, the structure of the tetrazolyl-based coordination complexes can be tailored by employing functionalysed tetrazoles in the assembly process [5], increasing the versatility and widening the applications of the tetrazole chemotype in coordination and supramolecular chemistry.…”

Section: Introductionmentioning

confidence: 99%

Insights into the photochemistry of 5-aminotetrazole derivatives with applications in coordination chemistry. Effect of the saccharyl moiety on the photostability

Ismael

Abe

Fausto

et al. 2019

Pure and Applied Chemistry

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The properties and applications of 2-methyl-(2H)-tetrazole-5-amino-saccharinate (2MTS) in catalysis and chelant-based chemotherapy stimulated investigations on its photostability. The photochemistry of monomeric 2MTS in solid argon (15 K) was compared with those of 2-methyl-(2H)-tetrazole-5-amine (2MT) and 1-methyl-(2H)-tetrazole-5-amine (1MT). Compounds were subjected to in situ narrowband UV-irradiation at different wavelengths. Reactions were followed by infrared spectroscopy, supported by B3LYP/6-311++G(d,p) calculations. Photochemical pathways for 2MT and 2MTS proved similar but photodegradation of 2MTS was 20× slower, unraveling the photostabilizing effect of the saccharyl moiety that extends into the nitrilimine formed from 2MTS and its antiaromatic 1H-diazirene isomer, which proved photostable at 290 nm, unlike the 1H-diazirene formed from 2MT. Analysis of the photochemistries of 2MTS/2MT (250 nm) and 1MT (222 nm), including energy trends calculated for the isomeric C2H5N3 species postulated/observed from photolysis and EPR results, enabled a deeper insight into the photodegradation mechanisms of 1,5-substituted and 2,5-substituted tetrazoles. We postulate a pivotal singlet state imidoylnitrene species, sN1, as common intermediate, which undergoes a Wolff-type isomerization to a stable carbodiimide. Photo-extrusion of N2 from 1,5-substituted tetrazoles generates sN1 directly but from 2,5-substituted tetrazoles it originates a nitrilimine, then a diazirene, which finally leads to sN1. Selective formation of cyanamide from 1MT requires photoisomerization between sN1 and sN2, accessible at 222 nm. EPR studies enabled the detection of methyl nitrene, arising from photolysis of 1H-diazirene intermediate.

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“…In this sense, azole compounds are considered promising organic ligands for the construction of MOFs due to their great diversity [ 3 , 4 ] and high coordination ability for bridging metal ions, providing strong metal–nitrogen interactions [ 5 , 6 , 7 , 8 ]. In addition, N -substituted azole compounds like N -substituted tetrazole heterocycles, can present intrinsically basic properties [ 9 ].…”

Section: Introductionmentioning

confidence: 99%

New URJC-1 Material with Remarkable Stability and Acid-Base Catalytic Properties

et al. 2016

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Abstract:Emerging new metal-organic structures with tunable physicochemical properties is an exciting research field for diverse applications. In this work, a novel metal-organic framework Cu(HIT)(DMF) 0.5 , named URJC-1, with a three-dimensional non-interpenetrated utp topological network, has been synthesized. This material exhibits a microporous structure with unsaturated copper centers and imidazole-tetrazole linkages that provide accessible Lewis acid/base sites. These features make URJC-1 an exceptional candidate for catalytic application in acid and base reactions of interest in fine chemistry. The URJC-1 material also displays a noteworthy thermal and chemical stability in different organic solvents of different polarity and boiling water. Its catalytic activity was evaluated in acid-catalyzed Friedel-Crafts acylation of anisole with acetyl chloride and base-catalyzed Knoevenagel condensation of benzaldehyde with malononitrile. In both cases, URJC-1 material showed very good performance, better than other metal organic frameworks and conventional catalysts. In addition, a remarkable structural stability was proven after several consecutive reaction cycles.

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Advances in synthesis of tetrazoles coordinated to metal ions

Abstract: The principal methods of synthesis of tetrazole-containing coordination complexes are systematized and generalized.

Cited by 30 publications

References 37 publications

5-(Azulen-1-yldiazenyl)tetrazoles; Syntheses and Properties

5-(Azulen-1-yldiazenyl)tetrazoles; Syntheses and Properties

Insights into the photochemistry of 5-aminotetrazole derivatives with applications in coordination chemistry. Effect of the saccharyl moiety on the photostability

New URJC-1 Material with Remarkable Stability and Acid-Base Catalytic Properties

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