- 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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- 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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- Protic ionic liquids: A lucid, rational tool for synthesis of phthalazinediones, quinoxalines and benzopyrans
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Protic ionic liquids (PILs), which are easily produced through the combination of a Bronsted acid and Bronsted base, such as [Mim]Ac and 1,4-diazabicyclo[ 2.2.2]octane (DABCO):AcOH:H2O (1:1:3), were found to be lucid, tunable tool for synthesis
- Mulik,Chandam,Patil,Patil,Mulik,Salunkhe,Deshmukh
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- Post synthesis alumination of KIT-6 materials with Ia3d symmetry and their catalytic efficiency towards multicomponent synthesis of 1H-pyrazolo[1,2-] phthalazine-5,10-dione carbonitriles and carboxylates
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Alumination of Si-KIT-6 materials with ordered three-dimensional (3D) structure were prepared by post-synthesis method with various Si/Al ratios. The catalysts were characterized by X-ray diffraction analysis (XRD), N2 porosimetry and FT-IR spectra. The presence of framework and extra framework aluminium was predicted by Aluminium MAS NMR. The strength of the acid sites of the catalysts was studied by NH3-TPD acidity measurements. The morphology of mesoporous materials was studied by SEM and TEM observation. The metal content of the samples was investigated by ICP-OES. The prepared solid acid catalysts were applied for the multi-component synthesis of 1H-pyrazolo[1,2-]phthalazine-5,10-diones from the reaction of phthalhydrazide, malononitrile/ethylcyano acetate and aromatic aldehyde in ethanol under liquid phase conditions. Activities of the catalysts follow the order: Al-KIT-6 (33) > Al-KIT-6 (56) > Al-KIT-6 (81) > Al-KIT-6 (110) > Nafion-H > Amberlyst-15 HM (12) > Hβ (8) > HY (4). The effects of reaction conditions and different catalysts have been studied. Various advantages associated with these protocols include effective catalysis, simple work-up procedure, short reaction times, high product yields, easy recovery and reusability of the catalysts.
- Karthikeyan,Pandurangan
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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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- Four-component synthesis of 3-amino-1-aryl-5,10-dioxo-1H-pyrazolo[1,2-b] phthalazine-2-carbonitrile derivatives promoted by potassium carbonate
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The one-pot, four-component reaction of phthalic anhydride, hydrazine hydrate, aromatic aldehydes and malononitrile afford 3-amino-1-aryl-5,10-dioxo-1H-pyrazolo[1,2-b]phthalazine-2-carbonitrile derivatives in the presence of potassium carbonate in ethanol under reflux conditions. These conditions offer simplified operation, easy purification, excellent yields and environmentally benign reaction conditions. Also, this method avoids the use of expensive catalysts, toxic solvents and chromatographic separation.
- Abdesheikhi, Mitra,Karimi-Jaberi, Zahed
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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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- 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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- Preparation, characterization, and first catalytic application of a novel phosphotungstic acid-containing ionic liquid immobilized on CuFe2O4@SiO2 magnetic nanoparticles in the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones
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A novel heterogeneous acidic ionic liquid based on functionalized imidazolium salt of phosphotungstic acid (H3PW12O40, denoted as PW), immobilized on CuFe2O4@SiO2 magnetic nanoparticles, denoted as CuFe2O4@SiO2@C3-Imid-C4SO3-PW, was prepared and characterized using FT-IR, SEM, EDX, and VSM techniques. High activity of the prepared material as a novel catalyst was evaluated in one-pot synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones by reaction of phthalhydrazide with an aromatic aldehyde and malononitrile under solvent-free conditions. The process gave high yields of the products over short reaction time. The catalyst was efficiently recovered by magnetic decantation and used repeatedly without significant loss of its activity.
- Hosseininasab,Davoodnia,Rostami-Charati,Khojastehnezhad
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- Ultrasound-assisted one-pot, three-component synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones
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Triethylamine was found to be an efficient catalyst for the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones by one-pot reaction of phthalhydrazide, aromatic aldehydes, and malononitrile or ethyl cyanoacetate in ethanol under ultrasonic irradiation. The advantages of this method are the use of an inexpensive and readily available catalyst, easy workup, improved yields, and the use of ethanol as a solvent that is considered to be relatively environmentally benign.
- Nabid, Mohammad Reza,Rezaei, Seyed Jamal Tabatabaei,Ghahremanzadeh, Ramin,Bazgir, Ayoob
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- Β-Cyclodextrin as a Supramolecular Catalyst for the Synthesis of 1H-Pyrazolo[1,2-b]phthalazine-5,10-dione Derivatives in Water
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Abstract: An efficient and green method has been developed for the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones derivatives by employing 20?mol% β-cyclodextrin via a one-pot multicomponent reaction of aldehydes, malononitrile and phthalhydrazide in H2O–EtOH (4:1) at 100 °C for first time under neutral condition. The catalyst could be recovered and reused for four consecutive cycles without appreciable loss in catalytic activity.
- Tayade, Yogesh A.,Dalal, Dipak S.
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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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- 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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- A convenient approach for the synthesis of various derivatives of pyrazolo[1,2-b]phthalazinediones in the presence of an efficient supported basic ionic liquid at ambient temperature and solvent-free media
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Abstract: A convenient procedure has been described for one-pot synthesis of various pyrazolo[1,2-b]phthalazinediones at ambient temperature and solvent-free media. First, a novel supported basic ionic liquid ([SiPMIM]OH@MNPs) was prepared and characterized by FT-IR, elemental analysis, VSM, SEM, TEM and XRD. This catalyst exhibits excellent catalytic activity in one-pot reaction of aromatic aldehydes, phthalhydrazide and malononitrile (or acyclic 1,3-dicarbonyl compounds) to offer cyano-, acetyl- or benzoyl-substituted pyrazolo[1,2-b]phthalazinediones in high yields. Moreover, selective synthesis of mono- and bis-pyrazolo[1,2-b]phthalazinediones from dialdehydes was investigated in this approach. The catalyst could be easily separated by an external magnet and reused seven times without any significant loss of activity. Graphical Abstract: An efficient procedure is described for one-pot synthesis of various cyano-, acetyl- or benzoyl-substituted pyrazolo[1,2-b]phthalazinediones in the presence of [SiPMIM]OH@MNPs at ambient temperature and solvent-free media.[Figure not available: see fulltext.].
- Hatami Sabour, Fereshteh,Nasr-Esfahani, Mahboobeh,Mohammadpoor-Baltork, Iraj,Tangestaninejad, Shahram,Moghadam, Majid,Mirkhani, Valiollah
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- CuO nanoparticles as a reusable catalyst for the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives under solvent-free conditions
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Nanostructured CuO was successfully utilized for the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives via one-pot multicomponent reaction among phthalhydrazide, malononitrile and aromatic aldehydes under solvent-free conditions. Utilization of non-toxic and inexpensive catalyst, improved yields in short reaction times, wide substrate scope and easy purification of products are the important features of the developed protocol. The CuO nanocatalyst presents good reusability over five catalytic cycles.
- Patil, Sonatai,Mane, Ananda,Dhongade-Desai, Savita
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- Synthesis of Fe3O4-supported Schiff base Cu (II) complex: a novel efficient and recyclable magnetic nanocatalyst for one-pot three-component synthesis of quinolin-5-one, chromene-3-carbonitrile and phthalazine-5,10-dione derivatives
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In this research, synthesis and characterization of a novel Schiff base Cu (II) complex immobilized on Fe3O4@SiO2 nanoparticles are reported. Then, the catalytic activity of these nanoparticles as magnetic recyclable nanocatalyst was explored for the one-pot three-component synthesis of quinolin-5-one, chromene-3-carbonitrile and phthalazine-5,10-dione derivatives. The reactions proceeded smoothly to provide the respective products in excellent yields under green conditions. Facile preparation of the catalyst, high yields of the products, low reaction times, and use of water as green solvent are the main advantages of the present protocol. Moreover, the catalyst can be easily separated from the reaction mixture in a magnetic field, recycled and reused for six consecutive fresh runs without considerable loss of catalytic activity. Graphic abstract: [Figure not available: see fulltext.]
- Ebrahimiasl, Hakimeh,Azarifar, Davood,Mohammadi, Mahsa,Keypour, Hassan,Mahmood abadi, Masoumeh
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- Urea-functionalized silica-coated Fe3?xTixO4magnetic nanoparticles: as highly efficient and recyclable heterogeneous nanocatalyst for synthesis of 4H-chromene and 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives
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Novel urea-functionalized silica-coated magnetic core–shell Fe3?xTixO4nanoparticles were prepared and fully characterized by different methods such as Fourier transform infrared spectroscopy, energy-dispersive X-ray spectr
- Azarifar, Davood,Badalkhani, Omolbanin,Abbasi, Younes,Hasanabadi, Morteza
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- Two Novel Pyrazole Derived Ionic Liquids Based on Chloride and Trichlorostannate Anions: Preparation, Characterization, and Evaluation of Their Catalytic Activity in the Synthesis of 1H-Pyrazolo[1,2-b]phthalazine-5,10-diones
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Abstract: Two novel room-temperature disulfonic acid functionalized ionic liquids derived from 3,5-dimethyl-1H-pyrazole consisting of chloride and trichlorostannate anions, 3,5-dimethyl-1,2-disulfonic acid-1H-pyrazolium chloride and 3,5-dimethyl-1,2-disul
- Vafaee,Davoodnia,Nakhaei,Yadegarian,Nejatianfar
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p. 273 - 278
(2021/03/19)
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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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- New role for photoexcited organic dye, Na2 eosin Y via the direct hydrogen atom transfer (HAT) process in photochemical visible-light-induced synthesis of spiroacenaphthylenes and 1H-pyrazolo[1,2-b]phthalazine-5,10-diones under air atmosphere
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A green multi-component tandem strategy for metal-free synthesizing spiroacenaphthylenes and 1H-pyrazolo[1,2-b]phthalazine-5,10-diones by Knoevenagel-Michael cyclocondensation is reported via organic dye Na2 eosin Y-derived photoexcited states functions as a direct hydrogen atom transfer (HAT) catalyst via visible light-mediated in aqueous ethyl lactate at ambient temperature under air atmosphere. This study paves the new role for further use of a metal-free organic dye with commercial availability and inexpensiveness, Na2 eosin Y in photochemical synthesis with use of the lowest amount of catalyst, energy-effectiveness, excellent yields, operational simplicity, time-saving aspects of the reaction and high atom economy, thus meeting some features of sustainable and green chemistry. Notably, this cyclization is also runnable on gram scale, which highlights the potentiality of using this reaction in industrial uses.
- Mohamadpour, Farzaneh
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- Catalyst-free, visible light irradiation promoted synthesis of spiroacenaphthylenes and 1H-pyrazolo[1,2-b]phthalazine-5,10-diones in aqueous ethyl lactate
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Catalyst-free three-component tandem approach can synthesize spiroacenaphthylenes and 1H-pyrazolo[1,2-b]phthalazine-5,10-diones by Knoevenagel-Michael cyclocondensation via visible light irradiation in aqueous ethyl lactate at room temperature. The signif
- Mohamadpour, Farzaneh
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- β-Alanine-functionalized magnetic graphene oxide quantum dots: an efficient and recyclable heterogeneous basic catalyst for the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione and 2,3-dihydroquinazolin-4(1H)-one derivatives
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In this research, we report a novel synthesis of magnetic β-alanine-functionalized-graphene oxide quantum dots Fe3O4@GOQDs-N-(β-alanine) as a recyclable and eco-friendly heterogeneous nanocatalyst. The catalytic efficiency of these nanosheets was explored as a basic catalyst for a one-pot three-component synthesis of various 1H-pyrazolo[1,2-b]phthalazine-5,10-dione and 2,3-dihydroquinazolin-4(1H)-one derivatives. The reactions proceeded smoothly under mild and green conditions to afford the respected products in excellent yields. The structure of this newly fabricated catalyst was successfully confirmed by different analytical techniques such as Fourier transform infrared spectroscopy, X-ray diffraction, field emission-scanning electron microscopy, high-resolution transmission electron microscopy, energy-dispersive X-ray spectroscopy, vibrating sample magnetometry, and thermogravimetric analysis. The stability and recyclability of the catalyst were examined by performing the model reaction in six consecutive runs. The recovered catalyst from the first run was directly used for the next runs with no significant loss of catalytic activity.
- Khaleghi Abbasabadi, Masoud,Azarifar, Davood
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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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- [Bu3NH][HSO4] catalyzed: an eco-efficient synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones and 2H-indazolo[2,1-b]phthalazine-triones under solvent-free conditions
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A Br?nsted acidic ionic liquid [Bu3NH][HSO4] as an eco-efficient catalyst for the one-pot multicomponent synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones and 2H-indazolo[2,1-b]phthalazine-triones by using various aldehyde, malo
- Shaikh, Mohd Akmal,Farooqui, Mazahar,Abed, Syed
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p. 5483 - 5500
(2018/08/22)
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- New racemic annulated pyrazolo[1,2-b]phthalazines as tacrine-like AChE inhibitors with potential use in Alzheimer's disease
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A novel series of tacrine-like compounds 7a-u possessing a fused pyrazolo[1,2-b]phthalazine structure were designed and synthesized as potent and selective inhibitors of AChE. The in-vitro biological assessments demonstrated that several compounds had hig
- Jalili-Baleh, Leili,Nadri, Hamid,Moradi, Alireza,Bukhari, Syed Nasir Abbas,Shakibaie, Mojtaba,Jafari, Mandana,Golshani, Mostafa,Homayouni Moghadam, Farshad,Firoozpour, Loghman,Asadipour, Ali,Emami, Saeed,Khoobi, Mehdi,Foroumadi, Alireza
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p. 280 - 289
(2017/08/14)
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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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- 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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p. 361 - 368
(2017/05/16)
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- Ionic liquid coated sulfonated carbon@titania composites for the one-pot synthesis of indeno[1,2-: B] indole-9,10-diones and 1 H -pyrazolo[1,2- b] phthalazine-5,10-diones in aqueous media
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A highly active and stable ionic liquid based novel solid Bronsted acid catalyst (C@TiO2-SO3H-ILs) was prepared by coating a long chain ionic liquid onto sulfonated carbon@titania composites. The ionic liquid coating resulted in efficient stability and activity of C@TiO2-SO3H-ILs under aqueous conditions by creating a hydrophobic environment on the catalyst surface. The catalytic activity of the newly designed catalyst was tested in the one-pot multicomponent synthesis of indeno[1,2-b]indole-9,10-diones and 1H-pyrazolo[1,2-b]phthalazine-5,10-diones in aqueous media. The structure of the most active catalyst, C@TiO2-SO3H-IL1, before and after the coating with the ionic liquid was investigated by FTIR, TGA, XRD, CHNS, EDX, SEM and HRTEM. The catalyst allows easy recovery and excellent reusability for up to five catalytic runs without considerable loss of activity.
- Kour, Manmeet,Bhardwaj, Madhvi,Sharma, Harsha,Paul, Satya,Clark, James H.
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p. 5521 - 5532
(2017/07/11)
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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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- An improved procedure for the three-component synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives using basic ionic liquid
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An efficient and green method for the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives has been achieved through the one-pot, three-component condensation of aromatic aldehydes, malononitrile or ethyl cyanoacetate, and phthalhydrazide in
- Wang, Wang,Cong-Hao, Li,Yi, Yu,Xiao-Jun, Li,Hong-Yun, Guo
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p. 354 - 357
(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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- Caesium carbonate supported on hydroxyapatite-encapsulated Ni0.5Zn0.5Fe2O4 nanocrystallites as a novel magnetically basic catalyst for the one-pot synthesis of pyrazolo[1,2-b]phthalazine-5,10-diones
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A novel nanomagnetic basic catalyst of caesium carbonate supported on hydroxyapatite-coated Ni0.5Zn0.5Fe2O4 magnetic nanoparticles (Ni0.5Zn0.5Fe2O4@HAP-Cs2CO3) was prepared. This new catalyst was fully characterized using Fourier transform infrared spectroscopy, transmission and scanning electron microscopy, X-ray diffraction and vibrating sample magnetometry techniques, and then the catalytic activity of this catalyst was investigated in the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives. Also, Ni0.5Zn0.5Fe2O4@HAP-Cs2CO3 could be reused at least five times without significant loss of activity and could be recovered easily by applying an external magnet. Thus, the developed nanomagnetic catalyst is potentially useful for the green and economic production of organic compounds.
- Maleki, Behrooz,Barat Nam Chalaki, Samaneh,Sedigh Ashrafi, Samaneh,Rezaee Seresht, Esmail,Moeinpour, Farid,Khojastehnezhad, Amir,Tayebee, Reza
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p. 290 - 295
(2015/04/27)
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- An efficient and high-yielding one-pot synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones catalyzed by sodium hydrogen carbonate under solvent-free conditions
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Sodium hydrogen carbonate, NaHCO3, efficiently catalyzes the one-pot, three-component reaction of phthalhydrazide, an aromatic aldehyde, and malononitrile or ethyl cyanoacetate under solvent-free conditions, to afford the corresponding 1H-pyraz
- Vafaee, Asieh,Davoodnia, Abolghasem,Pordel, Mehdi,Bozorgmehr, Mohammad Reza
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p. 2153 - 2158
(2016/02/27)
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- N,2-Dibromo-6-chloro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide: An efficient and homogeneous catalyst for one-pot synthesis of 4H-pyran, pyranopyrazole and pyrazolo[1,2-b]phthalazine derivatives under aqueous media
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N,2-Dibromo-6-chloro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide (DCDBTSD) as a highly efficient and homogeneous catalyst was successfully applied for the synthesis of 4H-pyran, pyranopyrazole and pyrazolo[1,2-b]phthalazine derivat
- Khazaei, Ardeshir,Zolfigol, Mohammad Ali,Karimitabar, Fatemeh,Nikokar, Iraj,Moosavi-Zare, Ahmad Reza
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p. 71402 - 71412
(2015/09/08)
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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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- A highly flexible green synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10- dione derivatives with CuI nanoparticles as catalyst under solvent-free conditions
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CuI nanoparticles as an efficient catalyst have been used for the preparation of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones by the four-component condensation reaction of phthalic anhydride, hydrazine monohydrate, aromatic aldehydes and malononitrile or ethyl cyanoacetate under solvent-free conditions in good to excellent yields, short reaction times and environmentally benign, milder reaction conditions.
- Safaei-Ghomi, Javad,Shahbazi-Alavi, Hossein,Ziarati, Abolfazl,Teymuri, Raheleh,Saberi, Mohammad Reza
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p. 401 - 405
(2014/03/21)
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- Synthesis of a diversified combinatorial library of 1H-pyrazolo[1,2-b] phthalazine-5,10-dione derivatives applying sustainable carbon-based solid acid catalyst involving a domino four-component reaction
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A SO3H-bearing carbonaceous solid catalyst has been synthesized through sulfonation followed by the hydrothermal carbonization method from renewable resource polyethylene glycol. The biodegradable catalyst was characterized by XRD, TEM, FT-IR, and energy dispersive X-ray. The surface area and pore diameter of the catalyst were determined by a nitrogen adsorption-desorption isotherm experiment. A highly efficient multicomponent heteroannulation protocol for the synthesis of a library of 1H-pyrazolo[1,2-b] phthalazine-5,10-dione derivatives has been developed by applying the solid acid catalyst. This synthesis was established to follow the group-assistant- purification chemistry process avoiding traditional chromatography. The aqueous reaction medium, easy recovery of the catalyst, and high yield of the products make the protocol attractive, sustainable, and economic. This work may not only lead to environmentally benign systems, but also will provide a new aspect of organic chemistry in water.
- Pradhan, Koyel,Paul, Sanjay,Das, Asish R.
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p. 1343 - 1352
(2014/07/22)
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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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- A rapid and an efficient route to the one-pot, multicomponent synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione ring systems
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CAN is found to be an efficient catalyst for the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives via one-pot coupling reaction of phthalhydrazide, aromatic aldehydes, and malononitrile or ethyl cyanoacetate in PEG as solvent. The major attributes of this synthetic protocol are the use of nontoxic, inexpensive, and readily available catalyst, mild conditions, easy work up, improved yields, and the PEG 400 as solvent that is environmentally benign as well as recyclable.
- Kidwai, Mazaahir,Chauhan, Ritika
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p. 1689 - 1696
(2015/01/09)
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- One-pot four-component synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10- dione derivatives
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The synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives by NiCl2-catalyzed novel one-pot four-component condensation reaction of phthalimide, hydrazine, malononitrile (or ethyl cyanoacetate), and aromatic aldehydes was reported. This work provides a simple, efficient, and eco-friendly method for the construction of pyrazolo[1,2-b]phalazine-5,10-dione derivatives.
- Song, Shi-Hua,Zhong, Jun,He, Yan-Hong,Guan, Zhi
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p. 7075 - 7077
(2013/01/15)
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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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- A highly efficient green synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10- dione derivatives and their photophysical studies
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A task-specific ionic liquid, [Bmim]OH, has been used for an efficient 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 under microwave irradiation. The advantages of this method include the use of green catalyst, no organic solvent, easy work-up and excellent yields. The photophysical properties for some 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives have been investigated for the first time.
- Raghuvanshi, Dushyant Singh,Singh, Krishna Nand
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experimental part
p. 5702 - 5705
(2011/11/04)
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- An efficient one-pot synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives
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An efficient, three-component, one-pot condensation reaction between phthalhydrazide, aromatic aldehydes, and malononitrile or ethyl cyanoacetate for the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives in excellent yields is reported. Ge
- Ghahremanzadeh, Ramin,Shakibaei, Ghazaleh Imani,Bazgir, Ayoob
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scheme or table
p. 1129 - 1132
(2009/04/04)
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