γ-Fe2O3@Si-(CH2)3@mel@(CH2)4SO3H as a magnetically bifunctional and retrievable nanocatalyst for green synthesis of benzo[c]acridine-8(9H)-ones and 2-amino-4H-chromenes

被引:17
作者
Karimirad, Fatemeh [1 ]
Behbahani, Farahnaz Kargar [1 ]
机构
[1] Islamic Azad Univ, Dept Chem, Karaj Branch, Karaj, Iran
关键词
gamma-Fe2O3@Si-(CH2)(3)@melamine@butyl sulfonic acid; nanoparticle; melamine; acridine; chromene; ONE-POT SYNTHESIS; SULFONIC-ACID; FE3O4; NANOPARTICLES; CLEAN PROCEDURE; CATALYST; EFFICIENT; DERIVATIVES; SPECTRA;
D O I
10.1080/24701556.2020.1802751
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The present work describes the synthesis and characterization of melamine functionalized with sulfonic acid supported on the magnetic nanoparticle, gamma-Fe2O3@Si-(CH2)(3)@melamine@butyl sulfonic acid nanoparticle as a green and retrievable bifunctional catalyst. This catalyst was assigned by FT-IR, XRD, EDX, TEM, VSM, CHN, and TGA analyses. In addition, the catalytic activity of this new catalyst was investigated for the synthesis of 7,10,11,12-tetrahydrobenzo[c]acridine-8(9H)-ones from aliphatic and aromatic aldehydes, dimedone and 1-naphthylamine in excellent yields and 2-amino-4H-chromenes were provided using manufactured nanocatalyst in good-to-high yield under mild reaction condition. The gamma-Fe2O3@Si-(CH2)(3)@melamine@butyl sulfonic acid heterogeneous catalyst showed the advantages such as very simple and eco-friendly due to use from magnetic nanoparticles as high reusability of the catalyst, magnetically separable catalyst, excellent yield, and mild reaction condition. The synthesis of some new derivatives of dibenzo[c]acridines and 2-amino-4H-chromenes in the presence of this nanocatalyst is also reported.
引用
收藏
页码:656 / 666
页数:11
相关论文
共 41 条
  • [1] Synthesis and application of melamine-based nano catalyst with phosphonic acid tags in the synthesis of (3′-indolyl)pyrazolo[3,4-b] pyridines via vinylogous anomeric based oxidation
    Afsar, Javad
    Zolfigol, Mohammad Ali
    Khazaei, Ardeshir
    Zarei, Mahmoud
    Gu, Yanlong
    Alonso, Diego A.
    Khoshnood, Abbas
    [J]. MOLECULAR CATALYSIS, 2020, 482
  • [2] Rational design, synthesis and biological evaluation of thiadiazinoacridines: A new class of antitumor agents
    Antonini, I
    Polucci, P
    Magnano, A
    Cacciamani, D
    Konieczny, MT
    Paradziej-Lukowicz, J
    Martelli, S
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (03) : 399 - 405
  • [3] EXPERIMENTAL SOLID TUMOR-ACTIVITY OF N-[2-(DIMETHYLAMINO)ETHYL]-ACRIDINE-4-CARBOXAMIDE
    BAGULEY, BC
    ZHUANG, L
    MARSHALL, E
    [J]. CANCER CHEMOTHERAPY AND PHARMACOLOGY, 1995, 36 (03) : 244 - 248
  • [4] Iron(iii) phosphate-catalyzed synthesis of 7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-ones
    Behbahani, F. K.
    Farahani, M.
    [J]. RUSSIAN CHEMICAL BULLETIN, 2015, 64 (01) : 151 - 153
  • [5] Behbahani F. K., 2013, GUJ SCI, V44, DOI [10.1002/chin.201340142, DOI 10.1002/CHIN.201340142]
  • [6] SYNTHESIS AND PHARMACOLOGICAL ACTIVITY OF 2-OXO-(2H) 1-BENZOPYRAN-3-CARBOXAMIDE DERIVATIVES
    BONSIGNORE, L
    LOY, G
    SECCI, D
    CALIGNANO, A
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1993, 28 (06) : 517 - 520
  • [7] Magnetic nanocatalysts: Synthesis and application in multicomponent reactions
    Chen, Meng-Nan
    Mo, Li-Ping
    Cui, Zhen-Shui
    Zhang, Zhan-Hui
    [J]. CURRENT OPINION IN GREEN AND SUSTAINABLE CHEMISTRY, 2019, 15 : 27 - 37
  • [8] SYNTHESIS AND SPECTRA OF 7-(ORTHO-R-PHENYL)-10,10-DIMETHYL-8,9,10,11-TETRAHYDROBENZ[C]ACRIDIN-8-ONES AND PARA-R-PHENYL)-10,10-DIMETHYL-8,9,10,11-TETRAHYDROBENZ[C]ACRIDIN-8-ONES - STRUCTURE CORRECTION OF 1,2,3,4-TETRAHYDRO-2,2-DIMETHYL-5-ARYL-6-AZA-7,8-BENZOPHENANTHREN-4-ONES
    CORTES, E
    MARTINEZ, R
    AVILA, JG
    TOSCANO, RA
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1988, 25 (03) : 895 - 899
  • [9] SYNTHESIS AND CARCINOGENIC ACTIVITY OF OXIDIZED BENZACRIDINES - POTENTIAL METABOLITES OF THE STRONG CARCINOGEN 7-METHYLBENZ[C]ACRIDINE AND OF THE INACTIVE ISOMER 12-METHYLBENZ[A]ACRIDINE
    CROISYDELCEY, M
    CROISY, A
    ZAJDELA, F
    LHOSTE, JM
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (02) : 303 - 306
  • [10] N,N-disulfo-1,1,3,3-tetramethylguanidinium carboxylate ionic liquids as reusable homogeneous catalysts for multicomponent synthesis of tetrahydrobenzo[a]xanthene and tetrahydrobenzo[a]acridine derivatives
    Dutta, Arup Kumar
    Gogoi, Pinky
    Saikia, Susmita
    Borah, Ruli
    [J]. JOURNAL OF MOLECULAR LIQUIDS, 2017, 225 : 585 - 591