Preparation and characterization of nanomagnetic piperidinium benzene-1,3-disulfonate ionic liquid as a novel, green and heterogeneous catalyst and its use in the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones and 1H-pyrazolo[1,2-a]pyridazine-5,8-diones under solvent-free conditions

被引:15
作者
Ghorbani-Vaghei, Ramin [1 ]
Mahmoodi, Jafar [1 ]
Maghbooli, Yaser [1 ]
机构
[1] Bu Ali Sina Univ, Fac Chem, Hamadan 6517838683, Iran
基金
美国国家科学基金会;
关键词
1H-pyrazolo[1,2-a]pyridazine-5,8-diones; 1H-pyrazolo[1,2-b]phthalazine-5,10-dione; magnetic nanoparticle ionic liquid (NMIL); piperidinium benzene-1,3-disulfonate; solvent-free conditions; ONE-POT PREPARATION; ANTIFUNGAL ACTIVITY; EFFICIENT CATALYST; REUSABLE CATALYST; ACID; DERIVATIVES; MILD; PARTICLES; MGO;
D O I
10.1002/aoc.3717
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The one-pot four-component synthesis of 1H-pyrazolo[1,2-b] phthalazine-5,10-diones and 1H-pyrazolo[1,2-a] pyridazine-5,8-diones was carried out from the reaction between various aldehydes, malononitrile, hydrazine hydrate and phthalic anhydride or maleic anhydride at 110 degrees C in solvent-free conditions using piperidinium benzene-1,3-disulfonate nanomagnetic ionic liquid (NMIL) as a novel and reusable catalyst. Some advantages of the presented procedure are a significant reduction in cost, effective catalysis and reusability of the catalyst. NMIL was thoroughly characterized using Fourier transform infrared spectroscopy, X-ray diffraction, scanning and transmission electron microscopies, thermogravimetry, derivative thermogravimetry, Brunauer-Emmett-Teller analysis, vibrating sample magnetometry and energy-dispersive X-ray spectroscopy. The technique is developed as a suitable and safe method for the synthesis of 1H-pyrazolo[1,2-b] phthalazine-5,10-diones and 1H-pyrazolo[1,2-a] pyridazine-5,8-diones making use of an efficient and reusable green catalyst.
引用
收藏
页数:10
相关论文
共 37 条
[1]  
Anadan S., 2006, J MOL CATAL A-CHEM, V256, P312
[2]   Nano-ZnO: an efficient and reusable catalyst for one-pot synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones and pyrazolo[1,2-a][1,2,4]triazole-1,3-diones [J].
Azarifar, Ali ;
Nejat-Yami, Razieh ;
Azarifar, Davood .
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2013, 10 (02) :297-306
[3]   3,4-DIPHENYL-1H-PYRAZOLE-1-PROPANAMINE ANTIDEPRESSANTS [J].
BAILEY, DM ;
HANSEN, PE ;
HLAVAC, AG ;
BAIZMAN, ER ;
PEARL, J ;
DEFELICE, AF ;
FEIGENSON, ME .
JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (02) :256-260
[4]   HYDROPHOBIC EFFECTS ON SIMPLE ORGANIC-REACTIONS IN WATER [J].
BRESLOW, R .
ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (06) :159-164
[5]   Efficient One-Pot Synthesis of Novell Spirooxindole Derivatives via Three-Component Reaction in Aqueous Medium [J].
Chen, Hui ;
Shi, Daqing .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2010, 12 (04) :571-576
[6]   Bifunctional nanocrystalline MgO for chiral epoxy ketones via Claisen-Schmidt condensation-asymmetric epoxidation reactions [J].
Choudary, BM ;
Kantam, ML ;
Ranganath, KVS ;
Mahendar, K ;
Sreedhar, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (11) :3396-3397
[7]  
Clark J.H., 2000, RSC CLEAN TECHNOL MO
[8]  
Gerard V.S., 2000, HETEROGENEOUS CATALY
[9]   One-pot synthesis of 1H-pyrazolo[1,2-b] phthalazine-5,10-dione derivatives under solvent-free conditions [J].
Ghorbani-Vaghei, Ramin ;
Noori, Samira ;
Toghraei-Semiromi, Zahra ;
Salimi, Zahra .
RSC ADVANCES, 2014, 4 (89) :47925-47928
[10]   Gold nanoclusters supported on MgO:: Synthesis, characterization, and evidence of Au6 [J].
Guzman, J ;
Gates, BC .
NANO LETTERS, 2001, 1 (12) :689-692