Sonochemical synthesis of chromenes catalyzed by L-phenyl alanine-attached nano-Fe3O4@SiO2

被引:2
作者
Safaei-Ghomi, Javad [1 ]
Eshteghal, Fahime [1 ]
Shahbazi-Alavi, Hossein [1 ]
机构
[1] Univ Kashan, Dept Organ Chem, Fac Chem, Kashan 87317, Iran
关键词
Chromenes; magnetic nanoparticles; core; shell; Fe3O4; ultrasonic irradiation; three-component condensation; ONE-POT SYNTHESIS; SOLVENT-FREE CONDITIONS; MULTICOMPONENT SYNTHESIS; ULTRASOUND IRRADIATION; ASSISTED SYNTHESIS; DERIVATIVES; EFFICIENT; NANOPARTICLES; NANOCATALYST; CHROMENE-6,8-DIONE;
D O I
10.1080/17518253.2018.1502819
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient multi-component synthesis of 10,10-dimethyl-7-(phenyl)-10,11-dihydrochromeno[4,3-b]chromene-6,8(7H,9H)-diones is described by a one-pot condensation reaction of aldehydes, dimedone and 4-hydroxycoumarin using L-phenyl alanine tethered to nano-Fe3O4@SiO2 under ultrasonic irradiation. The catalyst has been characterized by Fourier-transform infrared spectroscopy (FT-IR), X-ray powder diffraction (XRD), scanning electron microscope (SEM), Energy-dispersive X-ray spectroscopy (EDX), thermal gravimetric analysis (TGA) and vibrating-sample magnetometer (VSM). Atom economy, wide range of products, high catalytic activity, excellent yields in short reaction times, reusability of the catalyst and low catalyst loading are some of the important features of this protocol. [GRAPHICS]
引用
收藏
页码:345 / 351
页数:7
相关论文
共 42 条
[1]  
[Anonymous], 2016, RSC ADV, DOI DOI 10.1039/C6RA24029A
[2]   A novel sulfonic acid functionalized ionic liquid catalyzed multicomponent synthesis of 10,11-dihydrochromeno[4,3-b]chromene-6,8(7H,9H)-dione derivatives in water [J].
Chen, Zhiwei ;
Zhu, Qiang ;
Su, Weike .
TETRAHEDRON LETTERS, 2011, 52 (20) :2601-2604
[3]   Heck and Sonogashira cross-coupling reactions using recyclable Pd-Fe3O4 heterodimeric nanocrystal catalysts [J].
Chung, Jooyoung ;
Kim, Jinju ;
Jang, Youngjin ;
Byun, Sangmoon ;
Hyeon, Taeghwan ;
Kim, B. Moon .
TETRAHEDRON LETTERS, 2013, 54 (38) :5192-5196
[4]   Antimalarial activity of phenazines from lapachol, β-lapachone and its derivatives against Plasmodium falciparum in vitro and Plasmodium berghei in vivo [J].
de Andrade-Neto, VF ;
Goulart, MOF ;
da Silva, JF ;
da Silva, MJ ;
Pinto, MD ;
Pinto, AV ;
Zalis, MG ;
Carvalho, LH ;
Krettli, AU .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (05) :1145-1149
[5]   Hetero-annulated coumarins as new AChE/BuChE inhibitors: synthesis and biological evaluation [J].
Ebrahimi, Seyed Esmaeil Sadat ;
Ghadirian, Pegah ;
Emtiazi, Hamideh ;
Yahya-Meymandi, Azadeh ;
Saeedi, Mina ;
Mahdavi, Mohammad ;
Nadri, Hamid ;
Moradi, Alireza ;
Sameem, Bilqees ;
Vosooghi, Mohsen ;
Emami, Saeed ;
Foroumadi, Alireza ;
Shafiee, Abbas .
MEDICINAL CHEMISTRY RESEARCH, 2016, 25 (09) :1831-1841
[6]   Light from sonication of crystal slurries [J].
Eddingsaas, Nathan C. ;
Suslick, Kenneth S. .
NATURE, 2006, 444 (7116) :163-163
[7]  
Emtiazi H, 2014, S AFR J CHEM-S-AFR T, V67, P175
[8]  
Ghasemzadeh MA, 2015, ACTA CHIM SLOV, V62, P977
[9]  
Ghomi J. S., 2014, ACTA CHIM SLOV, V61, P703
[10]   Tandem Esterification/1,4-Addition-Type Friedel-Crafts Alkylation Reactions of Phenols/Naphthols with Olefinic Thioazlactones: Access to Functionalized 1,2-Dihydrobenzo[f]chromen-3-ones and 3,4-Dihydrochromen-2-ones [J].
Halimehjani, Azim Ziyaei ;
Khoshdoun, Maryam .
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (13) :5699-5704