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Mechanochemical Approach towards Multi-Functionalized 1,2,3-Triazoles and Anti-Seizure Drug Rufinamide Analogs Using Copper Beads

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Заглавие Mechanochemical Approach towards Multi-Functionalized 1,2,3-Triazoles and Anti-Seizure Drug Rufinamide Analogs Using Copper Beads
 
Автор Bhattacherjee, D.
Kovalev, I. S.
Kopchuk, D. S.
Rahman, M.
Santra, S.
Zyryanov, G. V.
Das, P.
Purohit, R.
Rusinov, V. L.
Chupakhin, O. N.
 
Тематика 1,2,3-TRIAZOLE
CLICK CHEMISTRY
CYCLOADDITION REACTION
MECHANOCHEMICAL SYNTHESIS
RUFINAMIDE SYNTHESIS
SOLVENT-FREE
ALKYNES
AZIDES
CATALYSIS
COPPER
TRIAZOLES
ALKYNE
AZIDE
COPPER
RUFINAMIDE
TRIAZOLE DERIVATIVE
CATALYSIS
CHEMISTRY
 
Описание Highly regiospecific, copper-salt-free and neat conditions have been demonstrated for the 1,3-dipolar azide-alkyne cycloaddition (AAC) reactions under mechanochemical conditions. A group of structurally challenging alkynes and heterocyclic derivatives was efficiently implemented to achieve highly functionalized 1,4-disubstituted-1,2,3-triazoles in good to excellent yield by using the Cu beads without generation of unwanted byproducts. Furthermore, the high-speed ball milling (HSBM) strategy has also been extended to the synthesis of the commercially available pharmaceutical agent, Rufinamide, an antiepileptic drug (AED) and its analogues. The same strategy was also applied for the synthesis of the Cl-derivative of Rufinamide. Analysis of the single crystal XRD data of the triazole was also performed for the final structural confirmation. The Cu beads are easily recoverable from the reaction mixture and used for the further reactions without any special treatment. © 2022 by the authors.
Ministry of Education and Science of the Russian Federation, Minobrnauka, (075-15-2022-1118)
This research was funded by the Ministry of Science and Higher Education of the Russian Federation (ref. # 075-15-2022-1118 dated 29 June 2022).
 
Дата 2024-04-08T11:06:39Z
2024-04-08T11:06:39Z
2022
 
Тип Article
Journal article (info:eu-repo/semantics/article)
Published version (info:eu-repo/semantics/publishedVersion)
 
Идентификатор Bhattacherjee, D, Kovalev, IS, Kopchuk, DS, Rahman, M, Santra, S, Zyryanov, GV, Das, P, Purohit, R, Rusinov, VL & Chupakhin, ON 2022, 'Mechanochemical Approach towards Multi-Functionalized 1,2,3-Triazoles and Anti-Seizure Drug Rufinamide Analogs Using Copper Beads', Molecules, Том. 27, № 22, 7784. https://doi.org/10.3390/molecules27227784
Bhattacherjee, D., Kovalev, I. S., Kopchuk, D. S., Rahman, M., Santra, S., Zyryanov, G. V., Das, P., Purohit, R., Rusinov, V. L., & Chupakhin, O. N. (2022). Mechanochemical Approach towards Multi-Functionalized 1,2,3-Triazoles and Anti-Seizure Drug Rufinamide Analogs Using Copper Beads. Molecules, 27(22), [7784]. https://doi.org/10.3390/molecules27227784
1420-3049
Final
All Open Access; Gold Open Access; Green Open Access
https://www.mdpi.com/1420-3049/27/22/7784/pdf?version=1668494028
https://www.mdpi.com/1420-3049/27/22/7784/pdf?version=1668494028
http://elar.urfu.ru/handle/10995/131327
10.3390/molecules27227784
85142641257
000887403000001
 
Язык en
 
Права Open access (info:eu-repo/semantics/openAccess)
cc-by
https://creativecommons.org/licenses/by/4.0/
 
Формат application/pdf
 
Издатель MDPI
 
Источник Molecules
Molecules