1044549-04-3

Basic information

• Product Name: ethyl 3-amino-1-(3-nitrophenyl)-5,10-dioxo-5,10-dihydro-1H-pyrazolo[1, 2-b]phthalazine-2-carboxylate
• Synonyms: ethyl 3-amino-1-(3-nitrophenyl)-5,10-dioxo-5,10-dihydro-1H-pyrazolo[1, 2-b]phthalazine-2-carboxylate
• CAS NO: 1044549-04-3
• Molecular Weight: 408.37
• Mol File: 1044549-04-3.mol

Chemical Properties

• CAS DataBase Reference: ethyl 3-amino-1-(3-nitrophenyl)-5,10-dioxo-5,10-dihydro-1H-pyrazolo[1, 2-b]phthalazine-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 3-amino-1-(3-nitrophenyl)-5,10-dioxo-5,10-dihydro-1H-pyrazolo[1, 2-b]phthalazine-2-carboxylate(1044549-04-3)
• EPA Substance Registry System: ethyl 3-amino-1-(3-nitrophenyl)-5,10-dioxo-5,10-dihydro-1H-pyrazolo[1, 2-b]phthalazine-2-carboxylate(1044549-04-3)

Safety Data

• Hazardous Substances Data: 1044549-04-3(Hazardous Substances Data)

Upstream product

• 1445-69-8 2,3-dihydrophthalazine-1,4-dione 
• 99-61-6 3-nitro-benzaldehyde 
• 105-56-6 ethyl 2-cyanoacetate 
• 85-44-9 phthalic anhydride 
• 136918-14-4 phthalimide 
• 88-96-0 phthalamide 

Relevant articles and documents

Efficient and convenient synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives mediated by L-proline

An efficient, four-component, one-pot condensation reaction of phthalimide or phthalic anhydride, aromatic aldehydes, and ethyl cyanoacetate for the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives mediated by L-proline in excellent yields is reported.

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

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.

Sio2:mgmno3: An efficient heterogeneous catalyst for one pot synthesis of 1h-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives

The present study deals with hydrothermal synthesis of SiO2 composite MgMnO3 catalyst. The obtained polycrystalline product was analyzed by using physical investigative techniques including XRD, SEM, EDAX, TEM, SAED and BET surface area. The product corresponded to average particle size of 100 nm by TEM images. The BET surface area was found 234.38 cm2/g for SiO2 composite MgMnO3 catalyst which indicates a good catalytic property. The synthesized catalyst was applied for the synthesis of 1H-pyrazolo[1,2-b]- phthalazine-5,10-dione in presence of ethanol as a solvent at 80°C. The current procedure and catalyst offers the gains of clean reaction, short reaction time, high yield, easy purification and financial availability of the catalyst.

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

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

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)

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

A rapid and an efficient route to the one-pot, multicomponent synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione ring systems

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.

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

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.

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

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.

A highly efficient green synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10- dione derivatives and their photophysical studies

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.