Introduction and characterization of a novel Cu(<sc>ii</sc>)-based quaternary deep eutectic solvent and its application in the efficient synthesis of triazoles and tetrazoles under mild conditions as an inexpensive, reusable, benign, and dual solvent/catalyst medium

被引:0
作者
Golestanifar, Laleh [1 ]
Sardarian, Ali Reza [1 ]
机构
[1] Shiraz Univ, Coll Sci, Chem Dept, Shiraz 84795, Iran
关键词
5-SUBSTITUTED; 1H-TETRAZOLES; PHYSICAL-PROPERTIES; 2+3 CYCLOADDITION; CHOLINE CHLORIDE; L-ARGININE; CATALYST; DERIVATIVES; CHEMISTRY; NITRILES;
D O I
10.1039/d4ra08090d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Deep eutectic solvents consist of hydrogen bond donor and acceptor components. They are a new type of ionic liquids, and they have attracted the attention of many chemists in recent years. In this work, a quaternary deep eutectic solvent (QDES) was prepared using choline chloride, glycerol, l-arginine, and copper acetate. Its physicochemical properties were determined by Fourier transform infrared spectroscopy (FT-IR), thermal analysis (TGA), differential scanning calorimetry (DSC), hydrogen potential (pH), cyclic voltammetry (CV), viscosity, density, refractive index, ionic conductivity and spectrophotometer ultraviolet-visible (UV-Vis). Further, as a novel benign solvent/catalyst for the synthesis of 1,4-disubstituted-1,2,3-triazole, 4-substituted-1H-1,2,3-triazole, and 5-substituted-1H-tetrazole derivatives were used in a click reaction strategy. The special features of this method include mild conditions, a non-toxic environment, short reaction time, easy operation, biodegradability, deep eutectic solvent/catalyst recovery, access to cheaper raw materials, and environmental compatibility.
引用
收藏
页码:3389 / 3405
页数:17
相关论文
共 40 条
[1]   1-Disulfo-[2,2-bipyridine]-1,1-diium chloride ionic liquid as an efficient catalyst for the green synthesis of 5-substituted 1 H-tetrazoles [J].
Aali, Elaheh ;
Gholizadeh, Mostafa ;
Noroozi-Shad, Nazanin .
JOURNAL OF MOLECULAR STRUCTURE, 2022, 1247
[2]   Fe3O4@L-lysine-Pd(0) organic-inorganic hybrid: As a novel heterogeneous magnetic nanocatalyst for chemo and homoselective [2+3] cycloaddition synthesis of 5-substituted 1H-tetrazoles [J].
Ashraf, Muhammad Aqeel ;
Liu, Zhenling ;
Li, Cheng ;
Zhang, Dangquan .
APPLIED ORGANOMETALLIC CHEMISTRY, 2021, 35 (03)
[3]   Sulfated tungstate a heterogeneous acid catalyst for synthesis of 4-aryl-NH-1,2,3-triazoles by 1,3-dipolar cycloaddition of nitroolefins with NaN3 [J].
Autade, Snehalata B. ;
Akamanchi, Krishnacharya G. .
SYNTHETIC COMMUNICATIONS, 2019, 49 (15) :1947-1956
[4]   A reusable polymer-supported copper(I) catalyst for triazole click reaction on water: An experimental and computational study [J].
Bahsis, Lahoucine ;
Ben El Ayouchia, Hicham ;
Anane, Hafid ;
Pascual-Alvarez, Alejandro ;
De Munno, Giovanni ;
Julve, Miguel ;
Stiriba, Salah-Eddine .
APPLIED ORGANOMETALLIC CHEMISTRY, 2019, 33 (04)
[5]   Thermal and physical properties of (Choline chloride plus urea plus L-arginine) deep eutectic solvents [J].
Chemat, Fareeda ;
Anjum, Hirra ;
Shariff, Azmi Md ;
Kumar, Perumal ;
Murugesan, Thanabalan .
JOURNAL OF MOLECULAR LIQUIDS, 2016, 218 :301-308
[6]   Effect of L-arginine on the physical properties of choline chloride and glycerol based deep eutectic solvents [J].
Chemat, Fareeda ;
You, Hor Jun ;
Muthukumar, Karuppan ;
Murugesan, Thanapalan .
JOURNAL OF MOLECULAR LIQUIDS, 2015, 212 :605-611
[7]   Assessing the greenness of some typical laboratory ionic liquid preparations [J].
Deetlefs, Maggel ;
Seddon, Kenneth R. .
GREEN CHEMISTRY, 2010, 12 (01) :17-30
[8]   Peanut shell as a green biomolecule support for anchoring Cu2O: a biocatalyst for green synthesis of 1,2,3-triazoles under ultrasonic irradiation [J].
Dolatkhah, Zahra ;
Mohammadkhani, Abolfazl ;
Javanshir, Shahrzad ;
Bazgir, Ayoob .
BMC CHEMISTRY, 2019, 13 (1)
[9]   Synthesis of 1,2,3-Triazole-Containing Methoxylated Cinnamides and Their Antileishmanial Activity against the Leishmania braziliensis Species [J].
dos Santos, Fabiola Suelen ;
de Freitas, Rossimiriam Pereira ;
de Freitas, Camila Simoes ;
Mendonca, Debora Vasconcelos Costa ;
Lage, Daniela Pagliara ;
Tavares, Grasiele de Sousa Vieira ;
Machado, Amanda Sanchez ;
Martins, Vivian Tamieti ;
Costa, Adilson Vidal ;
de Queiroz, Vagner Tebaldi ;
de Oliveira, Mariana Belizario ;
de Oliveira, Fabricio Marques ;
Antinarelli, Luciana Maria Ribeiro ;
Coimbra, Elaine Soares ;
Pilau, Eduardo Jorge ;
da Silva, Geovane Perez ;
Coelho, Eduardo Antonio Ferraz ;
Teixeira, Robson Ricardo .
PHARMACEUTICALS, 2023, 16 (08)
[10]   Synthesis and characterization of Cu-N, N′-Dicyclohexylcarbodiimide supported on CMK-3 as a novel, efficient and recoverable nanocatalyst for synthesis of tetrazole, polyhydroquinoline, and sulfoxide derivatives [J].
Ghafouri-Nejad, Raziyeh ;
Hajjami, Maryam .
REACTION KINETICS MECHANISMS AND CATALYSIS, 2020, 129 (01) :371-389