- DMAP as a new efficient catalyst for the one-pot synthesis of condensed phthalazines
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A new, convenient, and efficient method for the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones is developed starting from phthalhydrazide, aromatic aldehydes, and malononitrile using 4-N,N-dimethylaminopyridin as catalyst. This modified route provides much higher yields and a simple work-up procedure of products. Also this methodology is of interest due to the use of ethanol as a solvent without use of any toxic metals as catalyst, thus minimizing the cost, the operational hazards, and environmental pollution.
- Lamera, Esma,Bouacida, Sofiane,Merazig, Hocine,Chibani, Aissa,Le Borgne, Marc,Bouaziz, Zouhair,Bouraiou, Abdelmalek
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- Zeolite-based hybrid material as an efficient promoter in the green synthesis of mono/bis-phthalazinones
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Hybrid structures containing organic-inorganic porous materials are of great interest as green, heterogeneous, and recyclable catalysts. In this study, a novel organic-inorganic hybrid material (Zeolite HY@DETA) via the surface-functionalization of the Zeolite HY was prepared. The structure of hybrid material was characterized using the Fourier-transform infrared spectroscopy (FT-IR), field emission scanning electron microscopy (FE-SEM), Energy-dispersive X-ray spectroscopy (EDS), thermogravimetric analysis (TGA), and Brunauer–Emmett–Teller (BET) surface area analysis. Subsequently, the catalytic activity of this novel hybrid material was considered in the one-pot three-component synthesis of 3-amino-1-aryl-5,10-dioxo-1H-pyrazolo[1,2-b]phthalazine-2-carbonitrile and some bis phthalazine-dione derivatives under green and environmentally benign conditions. The products were synthesized in excellent yields within a short reaction time and identified using elemental analysis, FT-IR, 1H NMR, and 13C NMR spectroscopies. This protocol avoids the use of harmful catalysts, toxic solvents, and harsh reaction conditions. Besides, the catalyst could be recycled for five reaction runs with a slight loss of catalytic activity.
- Bodaghifard, Mohammad Ali,Ghasemi, Meisam,Hamidinasab, Mahdia
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supporting information
p. 3435 - 3448
(2021/09/29)
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- Mono- and bis-pyrazolophthalazines: Design, synthesis, cytotoxic activity, DNA/HSA binding and molecular docking studies
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In an attempt to find new potent cytotoxic compounds, several mono- and bis-pyrazolophthalazines 4a-m and 6a-h were synthesized through an efficient, one-pot, three- and pseudo five-component synthetic approach. All derivatives were evaluated for their in
- Hamidinasab, Mahdia,Ameri, Alieh,Hekmat, Azadeh,Forootanfar, Hamid,Mortezazadeh, Tohid,Bodaghifard, Mohammad Ali,Peytam, Fariba,Esmaeili, Rezvan,Foroumadi, Alireza,Sharifzadeh, Mohammad,Mobinikhaledi, Akbar,Khoobi, Mehdi
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- Experimental and DFT mechanistic insights into one-pot synthesis of 1: H -pyrazolo[1,2- b] phthalazine-5,10-diones under catalysis of DBU-based ionic liquids
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Benzylation of DBU followed by anion exchange of the resulting salt with trifluoroacetate gave nearly quantitatively the ionic liquid [Bn-DBU][TFA]. It is shown here to be an efficient catalyst for the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones via the three-component reaction of phthalhydrazide, aromatic aldehydes, and active α-methylene nitriles. DFT calculations at the B3LYP/SVP level and the experimental results are in agreement with a three-step mechanism for this reaction. Based on the DFT calculations, the catalytic effect largely arises from the intrinsic ionic properties of the ionic liquid rather than its action as a simple base. These calculations also predict the existence of two close-in-energy activated complexes whose rate determining roles and energies depend on their interaction with the anionic component of the ionic liquid, as [Bn-DBU][TFA] has shown a higher catalytic activity than [Bn-DBU][OAc]. This mechanistic approach opens up new and promising insights into the rational design of ionic liquid catalysts for the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones. The synthetic method presented here has several prominent advantages.
- Fallah-Ghasemi Gildeh, Sara,Mehrdad, Morteza,Roohi, Hossein,Ghauri, Khatereh,Fallah-Ghasemi Gildeh, Sahar,Rad-Moghadam, Kurosh
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p. 16594 - 16601
(2020/10/14)
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- Green synthesis of 1H-pyrazolo[1,2-b]phthalazine-2-carbonitrile derivatives using a new bifunctional base–ionic liquid hybrid magnetic nanocatalyst
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The ionic liquid-base N,N,2,2,6,6-hexamethyl-N-(3-(trimethoxysilyl)propyl)piperidin-4-amonium iodide was grafted onto titana-coated NiFe2O4 nanoparticles for obtaining an efficient and reusable ionic liquid-base hybrid nanocatalyst.
- Hamidinasab, Mahdia,Bodaghifard, Mohammad Ali,Mobinikhaledi, Akbar
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- Amelioration of H4[W12SiO40] by nanomagnetic heterogenization: For the synthesis of 1H–pyrazolo[1,2-b]phthalazinedione derivatives
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We conveniently coated silicotungstic acid (STA, H4[W12SiO40]) on amino-functionalized Si–magnetite nanoparticles, as surface functionalization of magnetic nanoparticles is an excellent way for green and efficient catalysis. The nanoparticles were structurally characterized using various techniques. The catalytic activity and recyclability of the STA–amine–Si–magnetite nanoparticles were probed through synthesis of 1H–pyrazolo[1,2-b]phthalazinedione derivatives. The reaction proceeds smoothly to provide products in excellent yields and short reaction times. The catalyst could be readily recovered using a simple external magnet and reused several times without any significant loss in activity. Herein, we report a comparison of the activity of H4[W12SiO40] as a homogeneous and heterogeneous catalyst, the latter being found to be more efficient. The findings offer effective methods for environmentally friendly synthesis of pyrazolo[1,2-b]phthalazinedione derivatives.
- Arora, Priya,Rajput, Jaspreet Kaur
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- Four-component clean process for the eco-friendly synthesis of 177-pyrazolo [1,2-b]phthalazine-5,10-dione derivatives using Zn(OAc)2.2H2O as an efficient catalyst under solvent-free conditions
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An efficient and convenient zinc acetate dihydrate (Zn(OAc)2.2H2O) catalyzed synthesis of li/-pyrazolo[l,2-b]phthalazine-5,10-dione derivatives has been accomplished via one-pot four-condensation of phthalic anhydride, hydrazine monohydrate, aromatic aldehydes derivatives and malononitrile under solvent-free conditions. The notable advantages of the present procedure are: operational simplicity, eco-friendly, environmentally benign nature, low-cost and non-toxic catalyst, no necessity of chromatographic purification steps, short reaction times and good to high yields.
- Mohamadpour, Farzaneh,Lashkari, Mojtaba,Heydari, Reza,Hazeri, Nourallah
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p. 843 - 851
(2019/05/21)
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- 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
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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?°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.
- Ghorbani-Vaghei, Ramin,Mahmoodi, Jafar,Maghbooli, Yaser
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- Preparation of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones using ZrO2 nanoparticles as a catalyst under solvent-free conditions
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Zirconium oxide nanoparticles are an efficient catalyst for the preparation of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones via a three-component reaction of phthalhydrazide, aromatic aldehydes and malononitrile under solvent-free conditions.
- Piltan, Mohammad
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p. 401 - 403
(2017/10/25)
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- Copper(II) acetate monohydrate: an efficient and eco-friendly catalyst for the one-pot multi-component synthesis of biologically active spiropyrans and 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives under solvent-free conditions
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Abstract: We have studied the catalytic ability of copper(II) acetate monohydrate as a mild, environmentally benign, natural and economical catalyst for the multi-component efficient synthesis of biologically active spiro-4H-pyran derivatives and 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives with excellent yields and short reaction times. The most important advantages of this procedure are its mild, non-toxic and inexpensive catalyst, one-pot synthesis, environmentally benign nature, solvent-free conditions, simple operational procedures, and highly efficient conditions. Graphical Abstract: [Figure not available: see fulltext.]
- Mohamadpour, Farzaneh,Maghsoodlou, Malek Taher,Heydari, Reza,Lashkari, Mojtaba
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p. 7841 - 7853
(2016/11/25)
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- Saccharin: a green, economical and efficient catalyst for the one-pot, multi-component synthesis of 3,4-dihydropyrimidin-2-(1H)-one derivatives and 1H-pyrazolo [1,2-b] phthalazine-5,10-dione derivatives and substituted dihydro-2-oxypyrrole
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Abstract: In this method, we have reported the catalytic ability of saccharin as a green, eco-friendly catalyst for the multi-component efficient synthesis of 3,4-dihydropyrimidin-2-(1H)-one derivatives and 1H-pyrazolo [1,2-b]phthalazine-5,10-dione derivatives and substituted dihydro-2-oxypyrrole with excellent yields and short reaction times. This present methodology has notable benefits such as green, inexpensive and non-toxic catalyst, one-pot, environmental benign nature, solvent-free conditions, simplicity of operation with no necessity of chromatographic purification steps and eco-friendly. Graphical Abstract: We have studied the catalytic ability of saccharin as a green, economical and environmentally benign nature for the multi-component efficient synthesis of 3,4-dihydropyrimidin-2-(1H)-ones derivatives, 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives and substituted dihydro-2-oxypyrrole with excellent yields and short reaction times. Green catalyst, mild, non-toxic, inexpensive, simple operational procedures, one-pot, high catalytic activity, eco-friendly, easily separated from the reaction mixture with no column chromatographic for the one-pot multi-component synthesis of these compounds are the most important advantages of this procedure.[Figure not available: see fulltext.]
- Mohamadpour, Farzaneh,Maghsoodlou, Malek Taher,Heydari, Reza,Lashkari, Mojtaba
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p. 1549 - 1560
(2016/07/06)
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- Ultrasound-assisted synthesis of pyrazolo[1,2-b]phthalazines and dihydrospiro[indoline-3,1'-pyrazolo[1,2-b]phthalazines] using TBAF as an efficient phase-transfer catalyst
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Tetrabutylammonim fluoride has been used as an efficient catalyst for synthesis of pyrazolo[1,2-b]-phthalazine-5,10-diones and dihydrospiro[indoline-3,1'-pyrazolo[1,2-b]phthalazines] by one-pot three-component reaction of phthalhydrazide, aromatic aldehyd
- Kefayati,Delafrooz,Homayoon
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p. 1735 - 1740
(2016/08/26)
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- Synthesis and characterization of dicationic 4,4′-bipyridinium dichloride ordered mesoporous silica nanocomposite and its application in the preparation of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives
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The sol-gel method was used for the synthesis of a dicationic 4,4′-bipyridine silica hybrid nanocomposite. In order to introduce 4,4′-bipyridine into the skeleton framework of an ordered mesoporous silica (SBA-15), first, the N,N′-bis(triethoxysilylpropyl)-4,4′-bipyridinium dichloride precursor was synthesized by the reaction of 3-chloropropyltriethoxysilane with 4,4′-bipyridine to give (TEOS)2BiPy2+ 2Cl-. The organic-inorganic hybrid nanocomposite, SBA@BiPy2+ 2Cl-, was then synthesized by the hydrolysis and polycondensation of the precursor and tetraethyl orthosilicate under mild acidic conditions. The nanocomposite was characterized by FT-IR spectroscopy, scanning electron microscopy (SEM), transmission electron microscopy (TEM), thermogravimetric analysis (TGA) and Brunauer-Emmett-Teller (BET). The characteristic results of FT-IR, XRD and TGA confirmed the coexistence of silica and 4,4′-bipyridinium dichloride networks. The catalytic ability of SBA@BiPy2+ 2Cl- as a novel environmentally safe heterogeneous nanoreactor for the preparation of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives via a one-pot multicomponent method under solvent-free conditions has been described. The catalyst can be reused without an obvious loss of catalytic activity.
- Bashti, Aigin,Kiasat, Ali Reza,Mokhtari, Babak
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p. 25816 - 25823
(2015/10/20)
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- Nano Br??nsted solid acid containing double-charged diazoniabi-cyclo[2.2.2]octane chloride supported on nano rice husk silica: An efficient catalyst for the one-pot synthesis of phthalazine compounds
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In the present work, amorphous silica nanoparticles were synthesized from low-cost rice husk ash (RH-SiO2). The nanoparticles were later modified by an acidic ionic liquid containing double-charged diazoniabi-cyclo[2.2.2]octane chloride using s
- Davarpanah, Jamal,Kiasat, Ali Reza
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p. 7986 - 7993
(2015/02/19)
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- Mild preparation of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives with magnetic Fe3O4 nanoparticles coated by (3-aminopropyl)-triethoxysilane as catalyst under ambient and solvent-free conditions
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An efficient, one-pot quantitative procedure for preparation of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives from four-component condensation reaction of hydrazine monohydrate, phthalic anhydride, malononitrile or ethyl cyanoacetate, and aromatic aldehydes in the presence of magnetic Fe3O4 nanoparticles coated by (3-aminopropyl)-triethoxysilane as catalyst under mild, ambient, and solvent-free conditions is described. Simple procedure, high yield, short reaction time, and environmentally benign method are advantages of this protocol. The magnetic Fe3O4 nanoparticles coated by (3-aminopropyl)-triethoxysilane can be recovered and reused several times without loss of activity.
- Shaterian, Hamid Reza,Mohammadnia, Majid
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p. 371 - 383
(2014/02/14)
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- Efficient One-Pot Solvent-Free Synthesis of 1H-Pyrazolo[1,2-b]phthalazine-5,10-diones Catalyzed by Sulfonic Acid Functionalized Nanoporous Silica (SBA-Pr-SO3H)
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A green protocol has been developed for the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones by one-pot cyclocondensation reaction of phthalhydrazide, aromatic aldehydes, and malononitrile or ethyl cyanoacetate using sulfonic acid functionalized SBA
- Ziarani, Ghodsi Mohammadi,Mohtasham, Nina Hosseini,Badiei, Alireza,Lashgari, Negar
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p. 990 - 994
(2016/02/18)
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- Electrocatalytic multicomponent assembling of phthalhydrazide, aldehydes and malononitrile: An efficient approach to 1H-pyrazolo[1,2-b]phthalazine-5,10- diones
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Electrocatalytic multicomponent transformation of phthalhydrazide, aromatic aldehydes and malononitrile in n-propanol in an undivided cell in the presence of sodium bromide as an electrolyte leads to 1H-pyrazolo[1,2-b]phthalazine-5,10- diones in short reaction times (4-8 min) and high yields (85-98%) at room temperature. The developed efficient electrocatalytic approach to the corresponding 1H-pyrazolo[1,2-b]phthalazine-5,10-diones is beneficial from the viewpoint of diversity-oriented large-scale processes and represents a new example of the ecologically pure synthetic concept for electrocatalytic multicomponent reactions strategy.
- Kefayati, Hassan,Amlashi, Shadi Homayoon,Kazemi-Rad, Reyhaneh,Delafrooz, Adeleh
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p. 894 - 898
(2014/08/18)
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- 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
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The catalytic activity of nano-structured ZnO has been explored in the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione and pyrazolo[1,2-a][1,2,4] triazole-1,3-dione derivatives via a three-component coupling reaction between aromatic aldehydes, malononitrile, and phthalhydrazides or 4-arylurazoles, respectively. High yield, low reaction times, non-toxicity and recyclability of the catalyst, and easy work-up are the main merits of this protocol. Graphical Abstract: [Figure not available: see fulltext.]
- Azarifar, Ali,Nejat-Yami, Razieh,Azarifar, Davood
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p. 297 - 306
(2013/07/26)
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- Mild basic ionic liquids catalyzed new four-component synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones
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A new four-component synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives using three weak basic ionic liquids such as 1,8-diazabicyclo[5.4.0] -undec-7-en-8-ium acetate, pyrrolidinium formate, and pyrrolidinium acetate as efficient catalysts for condensation reaction of hydrazine monohydrate, phthalic anhydride, malononitrile or ethyl cyanoacetate, and aromatic aldehydes under ambient and solvent-free conditions in excellent yields is described.
- Shaterian, Hamid Reza,Mohammadnia, Majid
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