Fe3O4@chitosan-tannic acid bionanocomposite as a novel nanocatalyst for the synthesis of pyranopyrazoles

被引:46
作者
Kamalzare, Maryam [1 ,2 ]
Ahghari, Mohammad Reza [2 ]
Bayat, Mohammad [1 ]
Maleki, Ali [2 ]
机构
[1] Imam Khomeini Int Univ, Fac Sci, Dept Chem, Qazvin, Iran
[2] Iran Univ Sci & Technol, Dept Chem, Catalysts & Organ Synth Res Lab, Tehran 1684613114, Iran
关键词
POT MULTICOMPONENT SYNTHESIS; MAGNETIC NANOPARTICLES; CATALYTIC APPLICATION; REUSABLE CATALYST; IONIC LIQUID; EFFICIENT; GREEN; DERIVATIVES; PYRAZOLE;
D O I
10.1038/s41598-021-99121-2
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
Recently magnetic nanocatalyst has attracted considerable attention because of its unique properties, including high performance, easy separation from the reaction mixture, and recyclability. In this study, a novel magnetic bionanocomposite was synthesized with chitosan and tannic acid as a natural material. The synthesized bionanocatalyst was characterized by essential analysis. Fe3O4@chitosan-tannic acid as a heterogeneous nanocatalyst was successfully applied to synthesize pyranopyrazole and its derivatives by a one-pot four-component reaction of malononitrile, ethyl acetoacetate, hydrazine hydrate, and various aromatic aldehyde. At the end of the reaction, the nanocatalyst was separated from the reaction mixture and was reused several times with no significant decrease in its catalytic performance. Simple purification of products, the ability for recovering and reusing the nanocatalyst, eco-friendliness, high yields of pure products, mild reaction conditions, short reaction time, non-toxicity, economically affordable are some of the advantages of using the fabricated nanocatalyst in the synthesis of pyranopyrazole.
引用
收藏
页数:10
相关论文
共 43 条
[21]   Green and efficient three-component synthesis of 4H-pyran catalysed by CuFe2O4@starch as a magnetically recyclable bionanocatalyst [J].
Kamalzare, Maryam ;
Bayat, Mohammad ;
Maleki, Ali .
ROYAL SOCIETY OPEN SCIENCE, 2020, 7 (07)
[22]   DABA MNPs: a new and efficient magnetic bifunctional nanocatalyst for the green synthesis of biologically active pyrano[2,3-c]pyrazole and benzylpyrazolyl coumarin derivatives [J].
Karami, Shahriar ;
Dekamin, Mohammad G. ;
Valiey, Ehsan ;
Shakib, Peyman .
NEW JOURNAL OF CHEMISTRY, 2020, 44 (33) :13952-13961
[23]   Catalyst-free domino reaction in water/ethanol: an efficient, regio- and chemoselective one-pot multi-component synthesis of pyranopyrazole derivatives [J].
Koohshari, Majid ;
Dabiri, Minoo ;
Salehi, Peyman .
RSC ADVANCES, 2014, 4 (21) :10669-10671
[24]   An Efficient Multi-component Synthesis of 6-Amino-3-methyl-4-Aryl-2,4-dihydropyrano[2,3-c]Pyrazole-5-carbonitriles [J].
Kumar, G. Santhosh ;
Kurumurthy, C. ;
Veeraswamy, B. ;
Rao, P. Sambasiva ;
Rao, P. Shanthan ;
Narsaiah, B. .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2013, 45 (05) :429-436
[25]   Magnetic nanoparticles:: Synthesis, protection, functionalization, and application [J].
Lu, An-Hui ;
Salabas, E. L. ;
Schueth, Ferdi .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (08) :1222-1244
[26]   Design and development of a new functionalized cellulose-based magnetic nanocomposite: preparation, characterization, and catalytic application in the synthesis of diverse pyrano[2,3-c]pyrazole derivatives [J].
Maleki, Ali ;
Eskandarpour, Vahid .
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2019, 16 (07) :1459-1472
[27]   Efficient one-pot four-component synthesis of 1,4-dihydropyridines promoted by magnetite/chitosan as a magnetically recyclable heterogeneous nanocatalyst [J].
Maleki A. ;
Kamalzare M. ;
Aghaei M. .
Journal of Nanostructure in Chemistry, 2015, 5 (1) :95-105
[28]   An efficient synthesis of benzodiazepine derivatives via a one-pot, three-component reaction accelerated by a chitosan-supported superparamagnetic iron oxide nanocomposite [J].
Maleki, Ali ;
Kamalzare, Maryam .
TETRAHEDRON LETTERS, 2014, 55 (50) :6931-6934
[29]   Fe3O4@cellulose composite nanocatalyst: Preparation, characterization and application in the synthesis of benzodiazepines [J].
Maleki, Ali ;
Kamalzare, Maryam .
CATALYSIS COMMUNICATIONS, 2014, 53 :67-71
[30]   Chitosan-supported Fe3O4 nanoparticles: a magnetically recyclable heterogeneous nanocatalyst for the syntheses of multifunctional benzimidazoles and benzodiazepines [J].
Maleki, Ali ;
Ghamari, Nakisa ;
Kamalzare, Maryam .
RSC ADVANCES, 2014, 4 (19) :9416-9423