73732-51-1Relevant articles and documents
Coupling ofN-tosylhydrazones with tetrazoles: synthesis of 2-β-d-glycopyranosylmethyl-5-substituted-2H-tetrazole type glycomimetics
Kaszás, Tímea,Cservenyák, Ivett,Juhász-Tóth, éva,Kulcsár, Andrea E.,Granatino, Paola,Nilsson, Ulf J.,Somsák, László,Tóth, Marietta
supporting information, p. 605 - 618 (2021/02/06)
Coupling reactions ofO-peracylated 2,6-anhydro-aldose tosylhydrazones (C-(β-d-glycopyranosyl)formaldehyde tosylhydrazones) with tetrazoles were studied under metal-free conditions using thermic or microwave activation in the presence of different bases. The reactions proved highly regioselective and gave the corresponding, up-to-now unknown 2-β-d-glycopyranosylmethyl-2H-tetrazoles in 7-67% yields. The method can be applied to get new types of disaccharide mimetics, 5-glycosyl-2-glycopyranosylmethyl-2H-tetrazoles, as well. Galectin binding studies withC-(β-d-galactopyranosyl)formaldehyde tosylhydrazone and 2-(β-d-galactopyranosylmethyl)-5-phenyl-2H-tetrazole revealed no significant inhibition of any of these lectins.
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.].
Piperazinium dihydrogen sulfate: An acidic ionic liquid for the [3+2] cycloaddition reaction of sodium azide with organic nitriles
Nowrouzi, Najmeh,Farahi, Soghra,Irajzadeh, Maryam
, p. 113 - 119 (2016/02/27)
Background: Tetrazoles are imperative nitrogen rich heterocyclic compounds with a wide range of applications in the field of organic synthesis, coordination chemistry, material sciences, and medicinal chemistry. A most common approach for the synthesis of 5-substituted-1H-Tetrazoles is achieved by [3+2] cycloaddition reaction of azides to nitriles. In this paper a new acidic ionic liquid is introduced as a catalyst to promote the mentioned reaction. Methods: Piperazinium dihydrogen sulfate:as a new acidic ionic compound was obtained by treatment of piperazine with sulfuric acid, which is further was applied as a catalyst for the [3+2] cycloaddition reaction of azides to organic nitriles. Results: The [3+2] cycloaddition reaction of sodium azide with structurally different organic nitriles using only 1.5 mol% of the piperazinium dihydrogen sulfate proceeded well at 100°C and 5-substituted-1H-Tetrazoles were prepared in good to excellent yields. Herein, piperazinium dihydrogen sulfate has a dual role of catalyst and reaction medium, which circumvents the use of any organic solvent. The catalyst is also recyclable. This method is particularly suitable for benzonitriles carrying deactivating groups which furnished the corresponding products in excellent yields. By this method, mono [3+2] cycloaddition product of dicyanides was obtained. Conclusion: In conclusion, piperazinium dihydrogen sulfate as a new acidic ionic compound was applied to promote synthesis of 5-substituted-1H-Tetrazoles through [3+2] cycloaddition reaction of organic nitriles with sodium azide. This new ionic compound can be easily separated from the reaction mixture which resulted to a simple work-up of the products.