An efficient synthesis of some new curcumin based pyrano[2,3-d] pyrimidine-2,4(3H)-dione derivatives using CoFe2O4@OCMC@Cu(BDC) as a novel and recoverable catalyst

被引:32
作者
Ghaffarian, Fatemeh [1 ]
Ghasemzadeh, Mohammad Ali [1 ]
Aghaei, Seyyed Soheil [2 ]
机构
[1] Islamic Azad Univ, Dept Chem, Qom Branch, Qom, Iran
[2] Islamic Azad Univ, Dept Microbiol, Qom Branch, Qom, Iran
关键词
Curcumin; Pyrano[2,3-d ]pyrimidine-2,4(3H)-dione; Metal-organic frameworks; CoFe2O4@OCMC@Cu(BDC); Catalyst; METAL-ORGANIC FRAMEWORKS; ONE-POT SYNTHESIS; MULTICOMPONENT SYNTHESIS; 3-COMPONENT SYNTHESIS; ANTIOXIDANT; ACID; NANOPARTICLES; MOFS;
D O I
10.1016/j.molstruc.2019.03.029
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
( )Curcumin (bis-alpha,beta-unsaturated beta-diketone) is a low molecular weight hydrophobic polyphenol isolated from Curcuma longa. Curcumin has attracted significant recent consideration due to its medicinal and pharmacological properties. In this research pyrano[2,3-d]pyrimidine-2,4(3H)-dione derivatives were prepared in excellent yields and short reaction times by a one-pot multi-component cyclocondensation of curcumin, substituted aromatic aldehydes and barbituric acid in the presence of CoFe2O4@OCMC@Cu(BDC) nanostructure as an effective and robust catalyst. The CoFe2O4 functionalized OCMC@Cu(BDC) is introduced as a new, strong and efficient catalyst for the synthesis of a variety of heterocyclic compounds. The catalyst was perfectly characterized by various spectroscopy methods such as Fouriertransform infrared spectroscopy (FT-IR), Energy-dispersive X-ray (EDX), Scanning electron microscope (SEM), X-ray diffraction (XRD) and N2 adsorption-desorption isotherm (BET). Furthermore, the heterocyclic compounds were fully characterized by different spectral techniques including FT-IR, (HNMR)-H-1, (CNMR)-C-13. The magnetic catalyst could be easily recycled and reused for seven runs with a slightly decrease in its activity. (C) 2019 Elsevier B.V. All rights reserved.
引用
收藏
页码:204 / 211
页数:8
相关论文
共 53 条
[1]  
[Anonymous], 2009, COORDIN CHEM REV, DOI DOI 10.1016/j.ccr.2009.05.019
[2]   Antifungal activity of turmeric oil extracted from Curcuma longa (Zingiberaceae) [J].
Apisariyakul, A ;
Vanittanakom, N ;
Buddhasukh, D .
JOURNAL OF ETHNOPHARMACOLOGY, 1995, 49 (03) :163-169
[3]   Synthesis, Characterization, Anticancer and Antibacterial Activity of Some Novel Pyrano[2,3-d]pyrimidinone Carbonitrile Derivatives [J].
Aremu, Oluwole S. ;
Gopaul, Kaalin ;
Kadam, Pramod ;
Singh, Moganavelli ;
Mocktar, Chunderika ;
Singh, Parvesh ;
Koorbanally, Neil A. .
ANTI-CANCER AGENTS IN MEDICINAL CHEMISTRY, 2017, 17 (05) :719-725
[4]   Diammonium hydrogen phosphate as a versatile and efficient catalyst for the one-pot synthesis of pyrano[2,3-d]pyrimidinone derivatives in aqueous media [J].
Balalaie, Saeed ;
Abdolmohammadi, Shahrzad ;
Bijanzadeh, Hamid Reza ;
Amani, Ali Mohammad .
MOLECULAR DIVERSITY, 2008, 12 (02) :85-91
[5]   One-Pot Synthesis of Pyrano[2,3-d]pyrimidinone Derivatives Catalyzed by L-Proline in Aqueous Media [J].
Bararjanian, M. ;
Balalaie, S. ;
Movassagh, B. ;
Amani, A. M. .
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2009, 6 (02) :436-442
[6]   Comparison of yield, composition, and antioxidant activity of turmeric (Curcuma longa L.) extracts obtained using various techniques [J].
Braga, MEM ;
Leal, PF ;
Carvalho, JE ;
Meireles, MAA .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2003, 51 (22) :6604-6611
[7]   PYRIDO[2,3-D]PYRIMIDINES .4. SYNTHETIC STUDIES LEADING TO VARIOUS OXOPYRIDO[2,3-D]PYRIMIDINES [J].
BROOM, AD ;
SHIM, JL ;
ANDERSON, GL .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (07) :1095-1099
[8]   Effect of sintering temperature on magnetization and Mossbauer parameters of cobalt ferrite nanoparticles [J].
Chandra, Grish ;
Srivastava, R. C. ;
Reddy, V. R. ;
Agrawal, H. M. .
JOURNAL OF MAGNETISM AND MAGNETIC MATERIALS, 2017, 427 :225-229
[9]   Metal-Organic Frameworks with Functional Pores for Recognition of Small Molecules [J].
Chen, Banglin ;
Xiang, Shengchang ;
Qian, Guodong .
ACCOUNTS OF CHEMICAL RESEARCH, 2010, 43 (08) :1115-1124
[10]   Industrial applications of metal-organic frameworks [J].
Czaja, Alexander U. ;
Trukhan, Natalia ;
Mueller, Ulrich .
CHEMICAL SOCIETY REVIEWS, 2009, 38 (05) :1284-1293