Synthesis and Application of Imidazolium-Based Ionic Liquid Supported on Hydroxyapatite Encapsulated γ-Fe2O3 Nanocatalyst in Preparation of Pyrido[2,3-d]Pyrimidines

被引:10
作者
Ramezanzadeh, Forough [1 ]
Mamaghani, Manouchehr [2 ]
Fallah-Bagher Shaidaei, Hossein [1 ]
Sheykhan, Mehdi [2 ]
机构
[1] Islamic Azad Univ, Rasht Branch, Fac Sci, Dept Chem, Rasht, Iran
[2] Univ Guilan, Fac Sci, Dept Chem, POB 41335-1914, Rasht, Iran
关键词
12-Dimethylimidazole; gamma-Fe2O3; HAp; ionic liquid; magnetic nanocatalyst; pyrido[23-d]pyrimidines; pyrrole; ONE-POT SYNTHESIS; HYBRID MAGNETIC NANOCATALYST; 5-SUBSTITUTED; 1H-TETRAZOLES; DERIVATIVES; COMPLEX; ACID; NANOPARTICLES; GREEN;
D O I
10.1080/10406638.2019.1705360
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthesis of novel 2-amino-5-aryl-7-(1-methyl-1H-pyrrol-2-yl)-4-oxo-3,4,5,8-tetrahydro-pyrido[2,3-d]pyrimidine-6-carbonitrile derivatives is reported by the reaction of 2,6-diaminopyrimidin-4(3H)-one, 3-(1-methy-1H-pyrrol-2-yl)-3-oxopropane nitrile and aryl aldehydes in the presence of newly synthesized imidazolium based ionic liquid supported on hydroxyapatite encapsulated gamma-Fe2O3 nanocatalyst [gamma-Fe2O3@HAp-Si(CH2)(3)Cl@DMIM] in short reaction times (7-13 min) and high to excellent yields (80%-95%). Cleaner reaction profile, mild reaction conditions, use of the green solvent and reusability of the catalyst, make this protocol attractive for the large scale synthesis of pyrido[2,3-d]pyrimidine-6-carbonitrile derivatives and is amenable for iterative combinatorial library generation. The synthesized nanoparticles were characterized by Fourier transform infrared spectroscopy, X-ray diffraction, scanning electron microscope, energy dispersive analysis of X-rays, thermogravimetric analysis, differential thermogravimetric and vibrating sample magnetometer.
引用
收藏
页码:1925 / 1943
页数:19
相关论文
共 50 条
[1]   One-pot synthesis of novel pyrido[2,3-d]pyrimidines using HAp-encapsulated-γ-Fe2O3 supported sulfonic acid nanocatalyst under solvent-free conditions [J].
Mohsenimehr, Moona ;
Mamaghani, Manouchehr ;
Shirini, Farhad ;
Sheykhan, Mehdi ;
Moghaddam, Fatemeh Azimian .
CHINESE CHEMICAL LETTERS, 2014, 25 (10) :1387-1391
[2]   An expeditious one-pot synthesis of novel bioactive indole-substituted pyrido[2,3-d]pyrimidines using Fe3O4@SiO2-supported ionic liquid nanocatalyst [J].
Mamaghani, Manouchehr ;
Sheykhan, Mehdi ;
Sadeghpour, Mahsa ;
Tavakoli, Fateme .
MONATSHEFTE FUR CHEMIE, 2018, 149 (08) :1437-1446
[3]   One-pot chemoselective synthesis of novel pyrrole-substituted pyrido [2,3-d]pyrimidines using [γ-Fe2O3@HAp-SO3FH] as an efficient nanocatalyst [J].
Jahanshahi, Parivash ;
Mamaghani, Manouchehr ;
Haghbin, Fereshteh ;
Nia, Roghayeh Hossein ;
Rassa, Mehdi .
JOURNAL OF MOLECULAR STRUCTURE, 2018, 1155 :520-529
[4]   Ionic Liquid as an Efficient and Recyclable Reaction Medium for the Synthesis of Pyrido[2,3-d]pyrimidines [J].
Du, Bai-Xiang ;
Li, Yu-Ling ;
Wang, Xiang-Shan ;
Shi, Da-Qing .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2013, 50 (03) :534-538
[5]   Poly(acrylic acid)/Fe3O4 supported on MIL-100(Cr) MOF as a novel and magnetic nanocatalyst for the synthesis of Pyrido[2,3-d]Pyrimidines [J].
Ghasemzadeh, Mohammad Ali ;
Mirhosseini-Eshkevari, Boshra .
HELIYON, 2022, 8 (08)
[6]   Introduction of a New Magnetic Nanocatalyst as an Organic-inorganic Hybrid Framework for the Synthesis of Pyrano[2,3-d]pyrimidinone(thione)s and Pyrido[2,3-d]pyrimidines [J].
Karimi-Chayjani, Reyhaneh ;
Daneshvar, Nader ;
Tajik, Hassan ;
Shirini, Farhad .
CHEMISTRYSELECT, 2019, 4 (04) :1205-1213
[7]   Application of 1-methyl imidazole-based ionic liquid-stabilized silica-coated Fe3O4 as a novel modified magnetic nanocatalyst for the synthesis of pyrano[2,3-d]pyrimidines [J].
Sajjadifar, Sami ;
Zolfigol, Mohammad Ali ;
Tami, Farzaneh .
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2019, 66 (03) :307-315
[8]   Synthesis of pyrano[2,3-d]pyrimidines and pyrido[2,3-d]pyrimidines in the magnetized deionized water based on UV-visible study [J].
Bakherad, Mohammad ;
Bagherian, Ghadamali ;
Rezaeifard, Amin ;
Mosayebi, Fatemeh ;
Shokoohi, Behzad ;
Keivanloo, Ali .
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2021, 18 (04) :839-852
[9]   An Expedient Synthesis of Novel Derivatives of Pyrido[2,3-d]pyrimidines Using Magnetically Supported ZrO2 Nanocatalyst [J].
Kheirkhah, Leila ;
Mamaghani, Manouchehr ;
Mahmoodi, Nosrat Ollah ;
Yahyazadeh, Asieh ;
Shojaei, Abdollah Fallah ;
Rostamli, Yaseman .
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2016, 63 (05) :410-416
[10]   [γ-Fe2O3@HAp-SO3H] an efficient nanocatalyst for the synthesis of highly functionalised 2-thioxopyrido[2,3-d]pyrimidines [J].
Mamaghani, Manouchehr ;
Taati, Zahra ;
Rasoulian, Mona ;
Yousefizad, Javad ;
Toraji, Nooshin ;
Mohsenimehr, Mona ;
Nia, Roghayeh Hossein .
JOURNAL OF CHEMICAL RESEARCH, 2016, (01) :29-34