82544-82-9Relevant academic research and scientific papers
Design and Synthesis of a BODIPY-Tetrazole Based “Off-On” in-Cell Fluorescence Reporter of Hydrogen Peroxide
An, Peng,Lewandowski, Tracey M.,Lin, Qing
, p. 1326 - 1333 (2018)
BODIPY-linked bithiophene-tetrazoles were designed and synthesized for bioorthogonal photoclick reactions in vitro and in vivo. The reactivity of these tetrazoles toward dimethyl fumarate was found to depend on the BODIPY attachment site, with the meta-linked BODIPY–tetrazole being the most reactive. The resulting pyrazoline cycloadduct showed drastically reduced BODIPY fluorescence. However, BODIPY fluorescence recovered after treatment with hydrogen peroxide. This turn-on effect was attributed to conversion from the pyrazoline to a pyrazole. Finally, we showed that this unique BODIPY–tetrazole off–on fluorescence probe can be used to detect hydrogen peroxide inside HeLa cells.
A robust and recyclable ionic liquid-supported copper(II) catalyst for the synthesis of 5-substituted-1H-tetrazoles using microwave irradiation
Padmaja,Chanda, Kaushik
, p. 1307 - 1317 (2019/11/14)
Abstract: A novel and robust ionic liquid-supported copper(II) catalyst has been developed and explored for the efficient synthesis of 5-substituted-1H-tetrazoles using microwave irradiation. The ionic liquid-supported catalyst facilitated the efficient isolation of tetrazole products with high purity by simple extraction with organic solvent. Recovered ionic liquid-supported copper(II) catalyst could be recycled for three times for the synthesis of tetrazole products with high purity. This synthetic protocol offers a very clean, convenient, and microwave-assisted environment-friendly method for the efficient synthesis of 5-substituted-1H-tetrazoles with high yield. Graphic abstract: [Figure not available: see fulltext.].
Highly active and reusable cu/c catalyst for synthesis of 5-substituted 1h-tetrazoles starting from aromatic aldehydes
Khalifeh, Reza,Khalili, Dariush,Rastegar, Najme
, p. 1044 - 1052 (2021/06/07)
A new, efficient and convenient method for the synthesis of 5-substituted 1H-tetrazole derivatives with a wide range of substituents in good to excellent yields has been developed. The synthesis was performed by the one-pot three-component [3+2]cycloaddit
One-Pot Suzuki-Hydrogenolysis Protocol for the Modular Synthesis of 2,5-Diaryltetrazoles
Bertrand, Sophie,Jamieson, Craig,Livingstone, Keith
, p. 7413 - 7423 (2020/07/07)
2,5-Diaryltetrazoles are a diverse range of compounds of considerable interest within the field of photochemistry as a valuable precursor of the nitrile imine 1,3-dipole. Current literature approaches toward this heterocycle remain unsuitable for the prac
HETEROCYCLIC COMPOUNDS AS FUNGICIDES
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Page/Page column 106, (2019/10/01)
The present invention relates to novel heterocyclic compound of Formula (I), (I) wherein, Het, L1, A, L2 and R12 are as defined in the detailed description, for use as fungicides.
Tetrazolylpropan-2-ones as inhibitors of fatty acid amide hydrolase: Studies on structure-activity relationships and metabolic stability
Garzinsky, David,Zahov, Stefan,Ekodo Voundi, Merlin,Hanekamp, Walburga,Lehr, Matthias
supporting information, p. 183 - 192 (2018/10/21)
A series of derivatives of 1-(4-octylphenoxy)-3-(2H-tetrazol-2-yl)propan-2-one (3) and 1-(4-octylphenoxy)-3-(1H-tetrazol-1-yl)propan-2-one (4) was synthesized and tested for fatty acid amide hydrolase (FAAH) inhibitory potency and phase I metabolic stability. Introduction of certain substituents like 4-chlorophenyl, 4-methoxycarbonylphenyl and carboxyl in position 5 of the tetrazole ring of 3 led to a significant increase of the metabolic stability of the scissile ketone pharmacophore, while the high activity towards FAAH was not affected markedly. In contrast, substituents in position 5 of the heterocyclic system of 4 did not have a considerable impact on the undesired ketone reduction. Furthermore, the effect of shielding the ketone group of some derivatives of 3 by a methyl substituent in position 3 of the propan-2-one scaffold and the consequences of the replacement of the lipophilic octyl residue of these compounds by more drug-like substituents were examined.
A Practical Synthesis of 5-Substituted 1 H -Tetrazoles from Aldoximes Employing the Azide Anion from Diphenyl Phosphorazidate
Ishihara, Kotaro,Kawashima, Mayumi,Matsumoto, Takatoshi,Shioiri, Takayuki,Matsugi, Masato
, p. 1293 - 1300 (2017/12/26)
5-Substituted 1 H -tetrazoles were effectively synthesized from aldoximes and diphenyl phosphorazidate (DPPA) under reflux conditions in xylenes. Various aldoximes underwent the cycloaddition reaction to afford the corresponding 5-substituted 1 H -tetrazoles in short reaction times and in good yields. Chiral aldoximes derived from amino acids also gave aminotetrazoles with almost no racemization.
[Cu(phen)(PPh3)2]NO3-catalyzed microwave-assisted green synthesis of 5-substituted 1H-tetrazoles
Padmaja,Meena,Maiti, Barnali,Chanda, Kaushik
, p. 7365 - 7374 (2017/09/06)
Abstract: An efficient synthetic methodology for construction of 5-substituted 1H-tetrazoles under microwave irradiation in green medium is described. With [Cu(phen)(PPh3)2]NO3 as catalyst and H2O-isopropyl alcohol (IPA) as reaction medium, various substituted nitriles underwent (3?+?2) cycloaddition reaction with NaN3 under microwave irradiation to provide corresponding 5-substituted 1H-tetrazoles in high yield. This method is not only efficient and general but also benefits from high functional group tolerance. This environmentally friendly synthetic methodology is visualized as an alternative to existing procedures, providing a simple route to privileged scaffolds.
Synthesis of 5-Substituted 1 H -Tetrazoles from Aldoximes Using Diphenyl Phosphorazidate
Ishihara, Kotaro,Kawashima, Mayumi,Shioiri, Takayuki,Matsugi, Masato
supporting information, p. 2225 - 2228 (2016/11/06)
A novel method for the synthesis of 5-substituted 1H-tetrazoles using diphenyl phosphorazidate (DPPA) has been developed. Aromatic and aliphatic aldoximes underwent cycloaddition to afford the corresponding 5-substituted 1H-tetrazoles with ease and efficiency.
Preparation of 5-substituted 1H-tetrazoles catalyzed by scandium triflate in water
Coca, Adiel,Turek, Evan,Feinn, Liana
, p. 218 - 225 (2015/11/02)
Several 5-substituted 1H-tetrazoles were prepared in water or isopropanol/water mixtures using microwave heating. Good yields were obtained for the [2 + 3] cycloaddition of sodium azide with aryl nitriles, aliphatic nitriles, and vinyl nitriles when catal
