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
• Article Data: 45

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

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

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

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

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.

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

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.

Green synthesis of 1H-pyrazolo[1,2-b]phthalazine-2-carbonitrile derivatives using a new bifunctional base–ionic liquid hybrid magnetic nanocatalyst

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.

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

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.].

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

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.]

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

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

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

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.