Fe3O4@Thiosemicarbazide-Cu(II): An efficient magnetically separable catalyst for greener synthesis of 1,2,3-triazoles using click reaction

被引:9
作者
Zond, Rutuja [1 ]
Yadav, Archana [1 ]
Yadav, Reshma [1 ]
Valekar, Navanath [2 ]
Pore, Santosh [3 ]
Chandam, Dattatraya [4 ]
Hangirgekar, Shankar [1 ]
Sankpal, Sandeep [1 ]
机构
[1] Shivaji Univ, Dept Chem, Kolhapur 416004, India
[2] Shivaji Univ, Dept Appl Chem, Kolhapur 416004, India
[3] Prof Dr ND Patil Mahavidyalaya, Dept Chem, Malakapur Perid 415101, India
[4] Bhogawati Mahavidyalaya Kurukali, Dept Chem, Bele 416001, India
关键词
Click chemistry; Heterogeneous catalyst; One-pot multicomponent reaction; 1,2,3-triazole; ONE-POT SYNTHESIS; REUSABLE NANOCATALYST; FE3O4; NANOPARTICLES; HIGHLY EFFICIENT; MULTICOMPONENT SYNTHESIS; BOEHMITE NANOPARTICLES; COUPLING REACTION; C-C; COPPER; DERIVATIVES;
D O I
10.1016/j.jorganchem.2023.122925
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
This work deals with the synthesis and characterization of a magnetically separable catalyst named Fe3O4@-Thiosemicarbazide-Cu(II) and its catalytic testing for the syntheses of 1,2,3-triazoles. The Fe3O4@Thiosemi-carbazide-Cu(II) was synthesized in three steps that involve the synthesis of magnetic iron oxide (Fe3O4), Fe3O4@Thiosemicarbazide, and complexation of Cu(II) on it. The new catalyst was fully characterized using various instrumental characterization techniques. The results revealed the formation of a stable catalyst with 17-22 nm in diameter. The catalyst was tested with the objective of presenting a new alternative way to synthesize 1,2,3-triazoles with improved and more efficient synthesis conditions. The catalytic efficiency of Fe3O4@Thiosemicarbazide-Cu(II) was evaluated for the synthesis of 1,2,3-triazoles via click reaction of terminal alkynes, alkyl halides, and sodium azide in aqueous ethanol (50:50 v/v) at 60 degrees C. The important features of the present methodology include excellent catalytic activity, use of green solvent, high yield, and facile separation of catalyst, shorter reaction time, and reusability of the catalyst. Therefore, the work and results obtained present clear significant advancements over the previously reported synthesis methods.
引用
收藏
页数:12
相关论文
共 61 条
[1]   Cu@CTF as an efficient heterogeneous catalyst in click reaction between azide and alkyne towards disubstituted triazoles [J].
Bhagat, Shivani ;
Dani, Shilpa ;
Verma, Ankit ;
Dharavath, Ravinder ;
Pratap, Umesh R. .
JOURNAL OF MOLECULAR STRUCTURE, 2023, 1284
[2]   Cellulose supported cuprous iodide nanoparticles (Cell-CuI NPs): a new heterogeneous and recyclable catalyst for the one pot synthesis of 1,4-disubstituted-1,2,3-triazoles in water [J].
Chavan, Pramod V. ;
Pandit, Kapil S. ;
Desai, Uday V. ;
Kulkarni, Makarand A. ;
Wadgaonkar, Prakash P. .
RSC ADVANCES, 2014, 4 (79) :42137-42146
[3]   Immobilization of Ni(ii) complex on the surface of mesoporous modified-KIT-6 as a new, reusable and highly efficient nanocatalyst for the synthesis of tetrazole and pyranopyrazole derivatives [J].
Darabi, Mitra ;
Nikoorazm, Mohsen ;
Tahmasbi, Bahman ;
Ghorbani-Choghamarani, Arash .
RSC ADVANCES, 2023, 13 (18) :12572-12588
[4]   Synthesis of Novel Triazole Incorporated Thiazolone Motifs Having Promising Antityrosinase Activity through Green Nanocatalyst CuI-Fe3O4@SiO2(TMS-EDTA) [J].
Darroudi, Mahdieh ;
Ranjbar, Sara ;
Esfandiar, Mohammad ;
Khoshneviszadeh, Mahsima ;
Hamzehloueian, Mahshid ;
Khoshneviszadeh, Mehdi ;
Sarrafi, Yaghoub .
APPLIED ORGANOMETALLIC CHEMISTRY, 2020, 34 (12)
[5]   Synthesis and evaluation of 1-alkyl-4-phenyl-[1,2,3]-triazole derivatives as antimycobacterial agent [J].
Gallardo, Hugo ;
Conte, Gilmar ;
Bryk, Fernando ;
Lourenco, Maria Cristina S. ;
Costa, Marilia S. ;
Ferreira, Vitor F. .
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2007, 18 (06) :1285-1291
[6]   Magnetic AgNPs/Fe3O4@chitosan/PVA nanocatalyst for fast one-pot green synthesis of propargylamine and triazole derivatives [J].
Ghasemi, Kousar ;
Darroudi, Mahdieh ;
Rahimi, Marjan ;
Rouh, Hossein ;
Gupta, Anju R. ;
Cheng, Chun ;
Amini, Abbas .
NEW JOURNAL OF CHEMISTRY, 2021, 45 (35) :16119-16130
[7]   C-P bond construction catalyzed by NiII immobilized on aminated Fe3O4@TiO2 yolk-shell NPs functionalized by (3-glycidyloxypropyl)trimethoxysilane (Fe3O4@TiO2 YS-GLYMO-UNNiII) in green media [J].
Ghasemzadeh, Maryam Sadat ;
Akhlaghinia, Batool .
NEW JOURNAL OF CHEMISTRY, 2019, 43 (14) :5341-5356
[8]   New Complex of Copper on Boehmite Nanoparticles as Highly Efficient and Reusable Nanocatalyst for Synthesis of Sulfides and Ethers [J].
Ghorbani-Choghamarani, Arash ;
Heidarnezhad, Zahra ;
Tahmasbi, Bahman .
CHEMISTRYSELECT, 2019, 4 (30) :8860-8869
[9]   Tribromide ion supported on boehmite nanoparticles as a reusable catalyst for organic reactions [J].
Ghorbani-Choghamarani, Arash ;
Seydyosefi, Zeinab ;
Tahmasbi, Bahman .
COMPTES RENDUS CHIMIE, 2018, 21 (11) :1011-1022
[10]   TEDETA@BNPs as a basic and metal free nanocatalyst for Knoevenagel condensation and Hantzsch reaction [J].
Ghorbani-Choghamarani, Arash ;
Heidarnezhad, Zahra ;
Tahmasbi, Bahman ;
Azadi, Gouhar .
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2018, 15 (10) :2281-2293