Modified magnetic chitosan with mono(6-amino-6-deoxy)-β-cyclodextrin as a novel catalyst toward the synthesis of pyrazolopyranopyrimidines and pyrano[2,3-c]pyrazole-3-carboxylates

被引:0
作者
Mousavi-Ebadi, Maryam [1 ]
Safaei-Ghomi, Javad [1 ]
机构
[1] Univ Kashan, Fac Chem, Dept Organ Chem, Kashan 8731751167, Iran
来源
SCIENTIFIC REPORTS | 2025年 / 15卷 / 01期
关键词
beta-Cyclodextrin; Magnetic Chitosan; Biocomposite; Nanocatalyst; Multi-component reaction; Pyrazole heterocycles; POT MULTICOMPONENT SYNTHESIS; BETA-CYCLODEXTRIN; GREEN APPROACH; EFFICIENT; WATER; PYRAZOLE; DERIVATIVES; ACID;
D O I
10.1038/s41598-025-92249-5
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
In this study, we successfully fabricated a novel biocomposite composed of 6-amino beta-cyclodextrin (CDNH2) grafted onto magnetic chitosan (Fe3O4@Cs). This biocomposite was thoroughly characterized using FT-IR, NMR, PXRD, EDX mapping, SEM, TEM, TGA, and VSM techniques. Subsequently, the innovative biocomposite was harnessed to serve as a heterogeneous catalyst to facilitate two series of multicomponent reactions (MCRs) aimed at synthesizing pyrazole-fused heterocycle derivatives. The first reaction involved the combination of hydrazine hydrate, ethyl 3-oxobutanoate, barbituric acid, and various benzaldehyde derivatives. In a separate reaction, dimethyl acetylenedicarboxylate (DMAD), hydrazine hydrate, benzaldehyde derivatives, and malonitrile were used as starting materials. By optimizing the reaction conditions and employing the Fe3O4@Cs@CDNH2 catalyst, we successfully synthesized valuable pyrazole structures with high yields in both reactions. The ability to optimize conditions and produce new pyrazole structures with impressive yields highlights the effectiveness of using Fe3O4@Cs@CDNH2 to direct these reactions.
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页数:19
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共 66 条
[1]  
Abid O., 2022, Colloids Surf. A: Physicochem Eng, V172, P1
[2]   Synthesis and characterization of Cu(II)-pyrazole complexes for possible anticancer agents; conformational studies as well as compatible in-silico and in-vitro assays [J].
Aljuhani, Enas ;
Aljohani, Meshari M. ;
Alsoliemy, Amerah ;
Shah, Reem ;
Abumelha, Hana M. ;
Saad, Fawaz A. ;
Hossan, Aisha ;
Al-Ahmed, Zehbah A. ;
Alharbi, Ahmed ;
El-Metwaly, Nashwa M. .
HELIYON, 2021, 7 (11)
[3]   Green Synthesis of Pyrazolo Pyrano Pyrimidine Derivatives Using ZnFe2O4/GA as a New Effective Catalyst in Water Media [J].
Amini, Haneye ;
Neamani, Shekofeh ;
Moradi, Leila .
CHEMISTRYSELECT, 2021, 6 (36) :9608-9615
[4]   Magnetic cobalt oxide supported organosilica-sulfonic acid as a powerful nanocatalyst for the synthesis of tetrahydrobenzo[a]xanthen-11-ones [J].
Ardeshirfard, Hakimeh ;
Elhamifar, Dawood .
SCIENTIFIC REPORTS, 2023, 13 (01)
[5]   Magnetic-propelled Fe3O4-chitosan carriers enhance l-asparaginase catalytic activity: a promising strategy for enzyme immobilization [J].
Ates, Burhan ;
Ulu, Ahmet ;
Koytepe, Suleyman ;
Ali Noma, Samir Abbas ;
Kolat, Veli Serkan ;
Izgi, Tekin .
RSC ADVANCES, 2018, 8 (63) :36063-36075
[6]   A review on chitosan and chitosan-based bionanocomposites: Promising material for combatting global issues and its applications [J].
Azmana, Motia ;
Mahmood, Syed ;
Hilles, Ayah Rebhi ;
Rahman, Azizur ;
Bin Arifin, Mohd Azmir ;
Ahmed, Shakeeb .
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, 2021, 185 :832-848
[7]   An efficient and green approach for the synthesis of 2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylates using Bi2O3/ZrO2 as a reusable catalyst [J].
Bhaskaruni, Sandeep V. H. S. ;
Maddila, Suresh ;
van Zyl, Werner E. ;
Jonnalagadda, Sreekantha B. .
RSC ADVANCES, 2018, 8 (29) :16336-16343
[8]   β-Cyclodextrin as a supramolecular catalyst for the synthesis of 2H-indazolo[2,1-b]phthalazine-trione derivatives in water and their antimicrobial activities [J].
Chate, Asha V. ;
Bhadke, Priyanka K. ;
Khande, Manisha A. ;
Sangshetti, Jaiprakash N. ;
Gill, Charansingh H. .
CHINESE CHEMICAL LETTERS, 2017, 28 (07) :1577-1582
[9]   Magnetic targeted nanoparticles based on β-cyclodextrin and chitosan for hydrophobic drug delivery and a study of their mechanism [J].
Chen, Pengfei ;
Song, Hang ;
Yao, Shun ;
Tu, Xianyu ;
Su, Miao ;
Zhou, Lu .
RSC ADVANCES, 2017, 7 (46) :29025-29034
[10]   Synthesis of magnetite nanoparticles-β-cyclodextrin complex [J].
Cobos Cruz, L. A. ;
Martinez Perez, C. A. ;
Monreal Romero, H. A. ;
Garcia Casillas, P. E. .
JOURNAL OF ALLOYS AND COMPOUNDS, 2008, 466 (1-2) :330-334