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Usage

Uses

Used in Organic Synthesis:
1-(3-NITROPHENYL)-1H-PYRROLE-2,5-DIONE is used as a versatile intermediate in organic synthesis for the preparation of a variety of chemical compounds.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 1-(3-NITROPHENYL)-1H-PYRROLE-2,5-DIONE is used as a building block for the creation of new drugs, leveraging its potential biological activities.
Used in Antimicrobial Applications:
1-(3-NITROPHENYL)-1H-PYRROLE-2,5-DIONE is studied for its antimicrobial properties, potentially serving as an agent against various microorganisms.
Used in Anticancer Research:
1-(3-NITROPHENYL)-1H-PYRROLE-2,5-DIONE is explored for its anticancer properties, indicating its potential use in cancer treatment and research.
Used in Organic Electronics:
Due to its photochemical properties, 1-(3-NITROPHENYL)-1H-PYRROLE-2,5-DIONE is considered for applications in the field of organic electronics, where it may contribute to the development of new electronic devices and materials.

InChI:InChI=1/C10H6N2O4/c13-9-4-5-10(14)11(9)7-2-1-3-8(6-7)12(15)16/h1-6H

Upstream product

• 99-09-2 3-nitro-aniline 
• 108-31-6 maleic anhydride 
• 36847-90-2 3-(3-nitro-phenylcarbamoyl)-acrylic acid 
• 42537-57-5 N-(3-nitrophenyl)maleamic acid 

Relevant academic research and scientific papers

Functional Porphyrinic Metal–Organic Framework as a New Class of Heterogeneous Halogen-Bond-Donor Catalyst

Biomimetic metal-organic frameworks have attracted great attention as they can be used as bio-inspired models, allowing us to gain important insights into how large biological molecules function as catalysts. In this work, we report the synthesis and utilization of such a metal-metalloporphyrin framework (MMPF) that is constructed from a custom-designed ligand as an efficient halogen bond donor catalyst for Diels–Alder reactions under ambient conditions. The implementation of fabricated halogen bonding capsule as binding pocket with high-density C?Br bonds enabled the use of halogen bonding to facilitate organic transformations in their three-dimensional cavities. Through combined experimental and computational studies, we showed that the substrate molecules diffuse through the pores of the MMPF, establishing a host-guest system via the C?Br???π interaction. The formation of halogen bonds is a plausible explanation for the observed boosted catalytic efficiency in Diels–Alder reactions. Moreover, the unique capability of MMPF highlights new opportunities in using artificial non-covalent binding pockets as highly tunable and selective catalytic materials.

Alizarin red S-TiO2-catalyzed cascade C(sp3)-H to C(sp2)-H bond formation/cyclization reactions toward tetrahydroquinoline derivatives under visible light irradiation

A very low amount of organic dye (Alizarin red S) sensitized TiO2 and it was successfully used to catalyze cascade C(sp3)-H to C(sp2)-H bond formation/cyclization reactions under visible light irradiation. The modified TiO2 photocatalyst efficiently, for the first time, advanced [4+2] cyclization of N,N-dimethylanilines and maleimides to the corresponding tetrahydroquinolines in air atmosphere. The reaction proceeds through α-amino radicals without additional oxidant at ambient temperature to afford products in good to excellent yields.

Catalyst and Additive-Free Diastereoselective 1,3-Dipolar Cycloaddition of Quinolinium Imides with Olefins, Maleimides, and Benzynes: Direct Access to Fused N,N′-Heterocycles with Promising Activity against a Drug-Resistant Malaria Parasite

A convenient and eco-friendly synthesis of various fused N-heterocyclic compounds through catalyst and additive-free 1,3 dipolar cycloadditions of quinolinium imides with olefins, maleimides, and benzynes in excellent yields and diastereoselectivities is reported. The thermally controlled diastereoselective [3 + 2] cycloaddition reaction between quinolinium imides and olefins provided cis-isomers at low temperature and trans-isomers at high temperature. A reaction between quinolinium imides with substituted maleimides gave four-ring-fused N-heterocyclic compounds in high yields as a single diastereomer. The aryne precursors also provided four-ring-fused N,N′-heterocyclic compounds in high yields. The in vitro antiplasmodial activity of selected molecules revealed that this class of molecules possesses potential for ongoing studies against malaria.

Solvent-free and room temperature visible light-induced C-H activation: CdS as a highly efficient photo-induced reusable nano-catalyst for the C-H functionalization cyclization of: T -amines and C-C double and triple bonds

Nano-sized CdS was successfully prepared, fully characterized and applied as a highly efficient reusable photocatalyst for the synthesis of pyrrolo[3,4-c]quinolone and pyrrolo[2,1-a]isoquinoline-8-carboxylate derivatives through a condensation reaction of N,N-dimethylanilines or alkyl 2-(3,4-dihydroisoquinolin-2(1H)-yl)acetates with maleimides via a C-H activation approach under benign and eco-friendly conditions at room temperature without using any solvent and oxidant under visible light irradiation. Besides, the prepared photocatalyst has been successfully applied for the condensation reaction of N,N-dimethylanilines with alkyl but-2-ynedioates or phenyl acetylenes for the synthesis of novel 1,2-dihydroquinoline-3,4-dicarboxylate and aryl-1,2-dihydroquinoline derivatives for the first time. Using this method, all favourable products were obtained in good yields and relatively short reaction times under benign conditions with the application of visible light irradiation, a renewable energy source. The catalyst was easily recovered and reused several times without any loss of its activity.

Graphene Oxide as a Carbocatalyst for a Diels–Alder Reaction in an Aqueous Medium

The Diels–Alder (DA) reaction, a [4+2] cycloaddition reaction, is highly important in synthetic organic chemistry and is frequently used in the synthesis of natural products containing six-membered rings. Herein, we report an efficient protocol for the DA reaction between 9-hydroxymethylanthracene and N-substituted maleimides using two-dimensional graphene oxide (GO) as a heterogeneous carbocatalyst in an aqueous medium at room temperature. High yields, a wide substrate scope, low temperature, excellent functional group tolerance, atom economy, and water as a green solvent are noteworthy features of this protocol. The heterogeneous GO catalyst can be easily recovered and used multiple times without any significant loss in catalytic activity.

Discovery and structural optimization of pyrazole derivatives as novel inhibitors of Cdc25B

Structural optimization and preliminary structure-activity relationship studies of a series of N-substituted maleimide fused-pyrazole analogues with Cdc25B inhibitory activity, starting from a high-throughput screening hit, are illustrated. A simplified 3,5-diacyl pyrazole analogue was obtained as the most potent compound (118, IC50 = 0.12 μM) with a 270-fold increase in potency.

Substituent chemical shifts of N-arylsuccinanilic acids, N-arylsuccinimides, N-arylmaleanilic acids, and N-arylmaleimides

NMR spectra of a series of N-arylsuccinanilic acids, N-arylsuccinimides, N-arylmaleanilic acids, and N-arylmaleimides were examined to estimate the electronic effect of the amide and imide groups on the chemical shifts of the hydrogen and carbon nuclei of the benzene ring.

Preparation, polymerization and characterization of some new maleimides

This article described the synthesis of poly N-arylmaleimides and copolymaleimides. The maleimides monomer N- (2-nitrophenyl)maleimide (2-NPMI), N-(3-nitrophenyl)maleimide (3-NPMI) and N-(4-nitrophenyl)maleimide (4-NPMI) were prepared from corresponding s

Cyanuric chloride: Decent dehydrating agent for an exclusive and efficient synthesis of kinetically controlled isomaleimides

Starting from maleanilic and maleamic acids, a facile general approach to kinetically controlled isomaleimides has been described for the first time using cyanuric chloride as a dehydrating agent with 85-98% yields. The effect of a variety of substituents