1044548-90-4

Basic information

• Product Name: 3-amino-1-(4-chlorophenyl)-5,10-dioxo-5,10-dihydro-1H-pyrazolo-[1,2-b]phthalazine-2-carbonitrile
• Synonyms: 3-amino-1-(4-chlorophenyl)-5,10-dioxo-5,10-dihydro-1H-pyrazolo-[1,2-b]phthalazine-2-carbonitrile
• CAS NO: 1044548-90-4
• Molecular Weight: 350.764
• Mol File: 1044548-90-4.mol

Chemical Properties

• CAS DataBase Reference: 3-amino-1-(4-chlorophenyl)-5,10-dioxo-5,10-dihydro-1H-pyrazolo-[1,2-b]phthalazine-2-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3-amino-1-(4-chlorophenyl)-5,10-dioxo-5,10-dihydro-1H-pyrazolo-[1,2-b]phthalazine-2-carbonitrile(1044548-90-4)
• EPA Substance Registry System: 3-amino-1-(4-chlorophenyl)-5,10-dioxo-5,10-dihydro-1H-pyrazolo-[1,2-b]phthalazine-2-carbonitrile(1044548-90-4)

Safety Data

• Hazardous Substances Data: 1044548-90-4(Hazardous Substances Data)

Upstream product

• 1445-69-8 2,3-dihydrophthalazine-1,4-dione 
• 104-88-1 4-chlorobenzaldehyde 
• 109-77-3 malononitrile 
• 85-44-9 phthalic anhydride 
• 88-96-0 phthalamide 
• 136918-14-4 phthalimide 

Relevant articles and documents

Mono- and bis-pyrazolophthalazines: Design, synthesis, cytotoxic activity, DNA/HSA binding and molecular docking studies

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

Preparation of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones using ZrO2 nanoparticles as a catalyst under solvent-free conditions

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.

Protic ionic liquids: A lucid, rational tool for synthesis of phthalazinediones, quinoxalines and benzopyrans

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

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

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.

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

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.

Four-component synthesis of 3-amino-1-aryl-5,10-dioxo-1H-pyrazolo[1,2-b] phthalazine-2-carbonitrile derivatives promoted by potassium carbonate

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.

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

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

Electrocatalytic multicomponent assembling of phthalhydrazide, aldehydes and malononitrile: An efficient approach to 1H-pyrazolo[1,2-b]phthalazine-5,10- diones

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.

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

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.

Ultrasound-assisted one-pot, three-component synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones

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.