Synthesis and characterization of Fe3O4@SiO2@(CH2)3NH(CH2)2O2P(OH)2 and its catalytic application in the synthesis of benzo-[h]quinoline-4-carboxylic acids via a cooperative anomeric based oxidation mechanism

被引:26
作者
Karimi, Fatemeh [1 ]
Yarie, Meysam [1 ]
Zolfigol, Mohammad Ali [1 ]
机构
[1] Bu Ali Sina Univ, Fac Chem, Dept Organ Chem, Hamadan 6517838683, Hamadan, Iran
基金
美国国家科学基金会;
关键词
2-Aminoethyl dihydrogen phosphate; Anomeric based oxidation; Synthesis of benzo-[h]quinoline-4-carboxylic acid; Fe3O4@SiO2@(CH2)(3)NH(CH2)(2)O2P(OH)(2); Multicomponent reactions; Nanomagnetic catalyst; ONE-POT SYNTHESIS; BIOLOGICAL EVALUATION; MULTICOMPONENT REACTIONS; MAGNETIC NANOPARTICLES; QUINOLINE ANALOGS; DERIVATIVES; NANOCATALYSTS; INHIBITORS; DESIGN; QUINAZOLINE;
D O I
10.1016/j.mcat.2020.110924
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
In this study, Fe3O4@SiO2@(CH2)(3)NH(CH2)(2)O2P(OH)(2) as a new and recoverable nanocatalyst with magnetic properties was synthesized. The characterization of the novel nanocatalyst confirmed by thermo gravimetric analysis/ differential thermal analysis (TGA/DTA), transmission electron microscopy (TEM), field emission scanning electron microscopy (FESEM) equipped by energy dispersive spectroscopy (EDS), elemental mapping analysis, Fourier transform infrared (FT-IR) spectroscopy and vibrating sample magnetometer (VSM). The impact of Fe3O4@SiO2@(CH2)(3)NH(CH2)(2)O2P(OH)(2) was carefully considered in the synthesis of benzo-[h]quinoline-4-carboxylic acids via a three component reaction of aryl aldehydes, naphtylamine, and pyrovic acid in the absence of solvent. The suggested mechanism proposed an anomeric based oxidation route for final step of the described synthesis. The described catalyst was recycled and reused without any remarkable decrease in the yield and the reaction time after six runs.
引用
收藏
页数:10
相关论文
共 60 条
[1]   A review on anticancer potential of bioactive heterocycle quinoline [J].
Afzal, Obaid ;
Kumar, Suresh ;
Haider, Md Rafi ;
Ali, Md Rahmat ;
Kumar, Rajiv ;
Jaggi, Manu ;
Bawa, Sandhya .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 97 :871-910
[2]  
Alabugin I. V., 2018, COMPUT MOL SCI, V9, pe1389
[3]  
Alabugin I. V., 2016, STEREOELECTRONIC EFF
[4]   Hyperconjugation [J].
Alabugin, Igor V. ;
Gilmore, Kerry M. ;
Peterson, Paul W. .
WILEY INTERDISCIPLINARY REVIEWS-COMPUTATIONAL MOLECULAR SCIENCE, 2011, 1 (01) :109-141
[5]   DEUTERIUM-ISOTOPE AND ANOMERIC EFFECTS IN THE CONFORMATIONAL EQUILIBRIA OF MOLECULES CONTAINING CHD-O GROUPS [J].
ANET, FAL ;
KOPELEVICH, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (08) :2109-2110
[6]  
[Anonymous], 2015, ADV HETEROCYCL CHEM
[7]   Copper Based Nanoparticles-Catalyzed Organic Transformations [J].
Babu, S. Ganesh ;
Karvembu, R. .
CATALYSIS SURVEYS FROM ASIA, 2013, 17 (3-4) :156-176
[8]   Novel photocatalyst: Titania-coated magnetite. Activity and photodissolution [J].
Beydoun, D ;
Amal, R ;
Low, GKC ;
McEvoy, S .
JOURNAL OF PHYSICAL CHEMISTRY B, 2000, 104 (18) :4387-4396
[9]   POTENTIAL ANTIMALARIALS - (2-PHENYL-7,8-BENZOQUINOLYL-4)-ALPHA-PIPERIDYLCARBINOLS [J].
BUCHMAN, ER ;
HOWTON, DR .
JOURNAL OF ORGANIC CHEMISTRY, 1949, 14 (05) :895-899
[10]   Magnetically recoverable nanoparticles as efficient catalysts for organic transformations in aqueous medium [J].
Cheng, Tanyu ;
Zhang, Dacheng ;
Li, Hexing ;
Liu, Guohua .
GREEN CHEMISTRY, 2014, 16 (07) :3401-3427