Green synthesis of 4,6-bisarylpyrimidin-2(1H)-ones and azo-linked 4-arylpyrimidin-2(1H)-ones using NiFe2O4@SiO2nPr@glucose amine as a mild nano catalyst

被引:7
作者
Nikpassand, Mohammad [1 ]
hoseinnezhad, Elaheh [2 ]
机构
[1] Islamic Azad Univ, Dept Chem, Rasht Branch, Rasht, Iran
[2] Ghadr Inst, Dept Chem, Rasht, Iran
关键词
Pyrimidin-2(1H)-one; NiFe2O4@(SiO2Pr)-Pr-n@glucose amine; Urea; Nanoparticle; Green synthesis; ONE-POT SYNTHESIS; MAGNETICALLY RECOVERABLE CATALYST; BIGINELLI REACTION; REUSABLE CATALYST; EFFICIENT; ACID; 3,4-DIHYDROPYRIMIDIN-2(1H)-ONES; PYRIMIDINES; FE3O4;
D O I
10.1016/j.arabjc.2020.10.022
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The clean, environmentally benign and effective synthesis of novel azo-linked 4-arylpyrimidin-2(1H)-one derivatives and 4,6-bisarylpyrimidin-2(1H)-ones via three-component reaction of various aldehydes or synthetized azo-linked aldehydes, urea, and acetophenone promoted by NiFe2O4@(SiO2Pr)-Pr-n@glucose amine at room temperature (25 degrees C) was reported. NiFe2O4@(SiO2Pr)-Pr-n@glucose amine were synthesized and characterized by transmission electron microscope (TEM), fourier transform infrared spectroscopy (FT-IR), vibrating sample magnetometry (VSM), X-ray powder diffraction (XRD) and X-ray spectroscopy (EDX). These compounds were obtained in high yields and short reaction times. The catalyst could be easily recovered and reused for six cycles with almost consistent activity. The structures of the synthesized 4,6-bisarylpyrimidin-2(1H)-one compounds were confirmed by H-1 NMR, C-13 NMR and FTIR spectral data and elemental analyses. (C) 2020 The Author(s). Published by Elsevier B.V. on behalf of King Saud University.
引用
收藏
页码:8995 / 9004
页数:10
相关论文
共 32 条
[1]  
Abaszadeh M, 2017, IRAN J CHEM CHEM ENG, V36, P35
[2]   "2-Amino glucose" as a substrate for synthesis of magnetically recoverable nanocatalyst NiFe2O4@SiO2@amino glucose for the green synthesis of novel bis (1,2-dihydro-4-hydroxy-2-oxoquinolin-3-yl)methanes [J].
Aghazadeh, Behnaz ;
Nikpassand, Mohammad .
CARBOHYDRATE RESEARCH, 2019, 483
[3]   A revision of the Biginelli reaction under solid acid catalysis. Solvent-free synthesis of dihydropyrimidines over montmorillonite KSF [J].
Bigi, F ;
Carloni, S ;
Frullanti, B ;
Maggi, R ;
Sartori, G .
TETRAHEDRON LETTERS, 1999, 40 (17) :3465-3468
[4]  
Chaudhari P.K., 2011, ADV DEV RES, V2, P54
[5]   Novel multi-component syntheses of pyrimidines using β-CD in aqueous medium [J].
Chowrasia, Rakhi ;
Katla, Ramesh ;
Darbem, Mariana P. ;
Branquinho, Tabata A. ;
de Oliveira, Aline Rufino ;
Manjari, Padma Sunitha ;
Domingues, Nelson Luis C. .
TETRAHEDRON LETTERS, 2016, 57 (15) :1656-1660
[6]   Searching for a direct preparation of dihydropyrimidine-5-carboxamides under Biginelli reaction conditions [J].
Couto, Irantzu ;
Tellitu, Imanol ;
Dominguez, Esther .
ARKIVOC, 2011, :115-126
[7]   Inhibition of hepatitis B virus replication by drug-induced depletion of nucleocapsids [J].
Deres, K ;
Schröder, CH ;
Paessens, A ;
Goldmann, S ;
Hacker, HJ ;
Weber, O ;
Krämer, T ;
Niewöhner, U ;
Pleiss, U ;
Stoltefuss, J ;
Graef, E ;
Koletzki, D ;
Masantschek, RNA ;
Reimann, A ;
Jaeger, R ;
Gross, R ;
Beckermann, B ;
Schlemmer, KH ;
Haebich, D ;
Rübsamen-Waigmann, H .
SCIENCE, 2003, 299 (5608) :893-896
[8]   Synthesis, characterization and antifungal testing of 3,4-dihydropyrimidin-2(1H)-(thio)ones containing boronic acids and boronate esters [J].
Duguay, Dominique R. ;
Zamora, Matthew T. ;
Blacquiere, Johanna M. ;
Appoh, Francis E. ;
Vogels, Christopher M. ;
Wheaton, Susan L. ;
Baerlocher, Felix J. ;
Decken, Andreas ;
Westcott, Stephen A. .
CENTRAL EUROPEAN JOURNAL OF CHEMISTRY, 2008, 6 (04) :562-568
[9]  
Ebraheem H.A., 2012, RAFIDAIN J S, V24, P120
[10]   Green, effective and chromatography free synthesis of benzoimidazo [1,2-a]pyrimidine and tetrahydrobenzo [4,5]imidazo [1,2-d]quinazolin-1(2H)-one and their pyrazolyl moiety using Fe3O4@SiO2@L-proline reusable catalyst in aqueous media [J].
Fekri, Leila Zare ;
Nikpassand, Mohammad ;
Khakshoor, Samira Nazari .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2019, 894 :18-27