Copper-carboxamide complex immobilized on nano NaY zeolite: an efficient catalyst for xanthenes synthesis

被引:4
作者
Younesi, Hamidreza [1 ]
Asghari, Sakineh [1 ]
Pasha, Ghasem Firouzzadeh [1 ]
Tajbakhsh, Mahmood [1 ]
机构
[1] Univ Mazandaran, Dept Organ Chem, Fac Chem, Babolsar 4741695447, Iran
关键词
Nano NaY zeolite; Ugi four-component reaction; Carboxamide-decorated nano NaY; Xanthenes; Green chemistry; SOLVENT-FREE SYNTHESIS; ACIDIC IONIC LIQUID; ONE-POT SYNTHESIS; MULTICOMPONENT REACTIONS; HIGHLY EFFICIENT; NANOPARTICLES; CONDENSATION; DERIVATIVES; ISOCYANIDE; DISCOVERY;
D O I
10.1007/s11164-023-05145-w
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This paper describes the direct synthesis of carboxamide-functionalized nano NaY zeolite (CBA-Ze) to develop a new high-functionality nanocatalyst in one pot process. This surface functionalization was achieved using a four-component Ugi reaction. Afterward, copper ions were coordinated with Ugi-ligands decorated on the nano NaY zeolite surface. To characterize the synthesized catalysts, fourier transform-infrared spectroscopy (FT-IR), thermogravimetric analysis (TGA), differential thermal analysis, scanning electron micrograph, transmission electron microscopy, X-ray diffraction (XRD), dynamic light scattering, energy dispersive spectroscopy, inductively coupled plasma, and elemental analyses were used. The nature of the supported Ugi-ligand on the zeolite's surface improved the catalyst reactivity of the zeolite, made it more homogeneous, and increased its ability to coordinate with copper ions. The catalytic activity of the synthesized copper-carboxamide complex immobilized on nano NaY zeolite (Cu@CBA-Ze) was investigated in the synthesis of Xanthen derivatives, resulting in product yields of 85-98% Cu@CBA-Ze using only 20 mg in H2O:EtOH (1:1) at room temperature within 30 min. In addition to the ease of recovering and reusing catalyst, and the simple setup procedure, this method is an eco-friendly, benign procedure for synthesizing heterocycles. This study describes a catalytic system with the potential to produce other useful heterocyclic compounds under mild environmental conditions.
引用
收藏
页码:5289 / 5313
页数:25
相关论文
共 64 条
[1]   Pulsed laser ablated zeolite nanoparticles: A novel nano-catalyst for the synthesis of 1,8-dioxo-octahydroxanthene and N-aryl-1,8-dioxodecahydroacridine with molecular docking validation [J].
Abdelghany, A. M. ;
Menazea, A. A. ;
Abd-El-Maksoud, Mansoura A. ;
Khatab, Tamer K. .
APPLIED ORGANOMETALLIC CHEMISTRY, 2020, 34 (02)
[2]   Efficient Fe3O4@TiO2 Composite Nanoparticles Catalyzed Synthesis of Novel Azo Xanthene Dyes with Promising Antimicrobial Activity [J].
Abdolmohammadi, Shahrzad ;
Hossaini, Zinatossadat ;
Azizi, Zahra .
CHEMISTRYSELECT, 2023, 8 (13)
[3]   Design, fabrication and characterization of magnetic nickel copper ferrite nanocomposites and their application as a reusable nanocatalyst for sonochemical synthesis of 14-aryl-14-H-dibenzo[a,j]xanthene derivatives [J].
Alipour, Azin ;
Naeimi, Hossein .
RESEARCH ON CHEMICAL INTERMEDIATES, 2023, 49 (06) :2705-2723
[4]   Synthesis and Characterization of New Dental Composite Containing Xanthene Based on Fish Bone Powder: Study on Anticancer and Antimicrobial Activity [J].
Amininasab, S. Mojtaba ;
Ghoseiri, Elham ;
Abdolmaleki, Sara .
MACROMOLECULAR RESEARCH, 2022, 30 (12) :891-899
[5]   Copper-amine complex immobilized on nano NaY zeolite as a recyclable nanocatalyst for the environmentally friendly synthesis of 2-amino-4H-chromenes [J].
Amiri, Mohammadreza Azizi ;
Pasha, Ghasem Firouzzadeh ;
Tajbakhsh, Mahmood ;
Asghari, Sakineh .
APPLIED ORGANOMETALLIC CHEMISTRY, 2022, 36 (12)
[6]   9-(4′-dimethylaminophenyl)-2,6,7-trihydroxy-xanthene-3-one is a Potentially Novel Antiplatelet Drug which Antagonizes the Effect of Thromboxane A2 [J].
Applova, Lenka ;
Veljovic, Elma ;
Muratovic, Samija ;
Karlickova, Jana ;
Macakova, Katerina ;
Zavrsnik, Davorka ;
Saso, Luciano ;
Duric, Kemal ;
Mladenka, Premysl .
MEDICINAL CHEMISTRY, 2018, 14 (02) :200-209
[7]   Amine modified nanozeolites for the three component synthesis of chromenes [J].
Babaei, Fatemeh ;
Asghari, Sakineh ;
Tajbakhsh, Mahmoud .
RESEARCH ON CHEMICAL INTERMEDIATES, 2019, 45 (09) :4693-4709
[8]   p-Sulfonic acid calix[4]arene as an efficient and reusable catalyst for the synthesis of acridinediones and xanthenes [J].
Baghbanian, Seyed Meysam ;
Khanzad, Gonja ;
Vahdat, Seyed Mohammad ;
Tashakkorian, Hamed .
RESEARCH ON CHEMICAL INTERMEDIATES, 2015, 41 (12) :9951-9966
[9]   4-hydroxycoumarin in heterocyclic synthesis -: Part III.: Synthesis of some new pyrano[2,3-d]pyrimidine, 2-substituted[1,2,4]triazolo[1,5-c]pyrimidine and pyrimido[1,6-b][1,2,4]triazine derivatives [J].
Bedair, AH ;
El-Hady, NA ;
Abd El-Latif, MS ;
Fakery, AH ;
El-Agrody, AM .
FARMACO, 2000, 55 (11-12) :708-714
[10]  
Bhale PS., 2015, Chem. Sci. Trans, V4, P246