19171-27-8

Usage

Uses

Used in Pharmaceutical Research:
2-(pyridin-3-yl)-1H-isoindole-1,3(2H)-dione is used as a building block in pharmaceutical research for its potential therapeutic applications. It is particularly noted for its investigation as an anti-cancer agent, where it may contribute to the development of novel treatments targeting various types of cancer.
Used in the Treatment of Neurodegenerative Diseases:
In the medical field, 2-(pyridin-3-yl)-1H-isoindole-1,3(2H)-dione is also considered for its potential role in the treatment of neurodegenerative diseases, suggesting that it could be instrumental in managing or alleviating symptoms associated with such conditions.
Used in Organic Synthesis:
As a component in organic synthesis, 2-(pyridin-3-yl)-1H-isoindole-1,3(2H)-dione is utilized for the creation of new chemical entities, leveraging its reactivity and structural features to synthesize complex organic compounds.
Used in Fluorescent Probes and Organic Electronics:
2-(pyridin-3-yl)-1H-isoindole-1,3(2H)-dione is used as a component in the development of fluorescent probes, which are essential tools in biological and chemical research for visualizing and tracking specific molecules or processes. Additionally, its potential application in organic electronics highlights its versatility in contributing to the advancement of electronic materials and devices.

Upstream product

• 462-08-8 pyridin-3-ylamine 
• 85-44-9 phthalic anhydride 
• 615-42-9 1,2-Diiodobenzene 
• 201230-82-2 carbon monoxide 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 110-86-1 pyridine 
• 3481-09-2 N-chlorophthalimide 
• 5672-90-2 N-(trifluoromethyl)acyloxyphthalimide 
• 524-38-9 N-hydroxyphthalimide 
• 88-67-5 2-Iodobenzoic acid 
• 521-73-3 isoquinoline-1,3,4-trione 

Downstream Products

• 1191083-49-4 [Au(PPh₃)(3-amino-N-phthalimidopyridine)](OTf) 

Relevant academic research and scientific papers

Syntheses, structural studies and spectroscopic characterisation of pyridyl-phthalimide complexes of fac-(CO)3ReI-diimines

The mono-dentate ligands, 3-aminomethyl-N-phthalimido-pyridine (L1) and 3-amino-N-phthalimido-pyridine (L2), were synthesised using a solvent-free melt method. These ligands were then used to access three pairs of functionalised lumi

On the Photochemical Reactivity of Phthalonimide

The occurence of an electrophilic phthalonimidyl radical is proposed to account for the N-arylation products obtained by irradiation of phthalonimide in benzene in the presence of an amine and oxygen.Normal carbonyl reactivity is observed in the photochemical reactions of phthalonimide with furan (oxetane formation) and hydrogen donors (photoreduction).

Nitrogen-centered radical-mediated C-H imidation of arenes and heteroarenes via visible light induced photocatalysis

The C-H imidation of arenes and heteroarenes has been achieved via visible light induced photocatalysis. In the presence of an iridium(iii) photoredox catalyst, the reaction of aromatic substrates with N-chlorophthalimide furnishes the N-aryl products at room temperature through a nitrogen-centered radical mediated aromatic substitution.

N-acyloxyphthalimides as nitrogen radical precursors in the visible light photocatalyzed room temperature C-H amination of arenes and heteroarenes

This paper reports a room temperature visible light photocatalyzed method for the C-H amination of arenes and heteroarenes. A key enabling advance in this work is the design of N-acyloxyphthalimides as precursors to nitrogen-based radical intermediates for these transformations. A broad substrate scope is presented, including the selective meta-amination of pyridine derivatives. A radical aromatic substitution mechanism is proposed.

Immobilized palladium metal containing ionic liquid catalyzed one step synthesis of isoindole-1,3-diones by carbonylative cyclization reaction

Immobilized palladium metal containing ionic liquid (ImmPd-IL) catalyzed carbonylative cyclization reaction of 2-iodobenzoic acid and primary amine provided N-substituted isoindole-1,3-dione derivatives in good to excellent yield. The influence of various reaction parameters including the effect of base, solvent, temperature, time and CO pressure on carbonylative cyclization reaction using ImmPd-IL catalyst was investigated. Using optimized reaction parameters different aromatic, aliphatic and heterocyclic N-substituted isoindole-1,3-dione derivatives were synthesized from corresponding aryl amines. The developed protocol is heterogeneous, phosphine free and requires attainable reaction conditions like atmospheric CO pressure and lesser reaction time. The scope of the developed protocol was also extended for the synthesis of N-substituted isoindole-1,3-diones from methyl-2-iodobenoate and 1,2-diiodo benzene. The ImmPd-IL catalyst was recyclable up to four consecutive cycles and recycled catalyst was characterized by XPS analysis.

Palladium on carbon: An efficient, heterogeneous and reusable catalytic system for carbonylative synthesis of N-substituted phthalimides

The application of palladium on carbon (Pd/C) as a heterogeneous recyclable catalyst was investigated for the double carbonylation of o-dihaloarenes with amines providing excellent yield of N-substituted phthalimides in shorter reaction time as compared to earlier reported homogeneous protocols. Furthermore, the scope of the developed protocol was applied for the synthesis N-substituted phthalimides from o-halobenzoates and o-halobenzoic acid via a single step carbonylative cyclization reaction. The developed methodology describes an efficient one-step approach for the synthesis of an important class of heterocycles and tolerates a wide variety of functional groups. It circumvents the use of phosphine ligands with an additional advantage of catalyst recyclability for up to eight consecutive cycles. Copyright

New anti-inflammatory N-pyridinyl(alkyl)phthalimides acting as tumour necrosis factor-α production inhibitors

This paper describes the synthesis of N-pyridinyl(alkyl)phthalimides related to N-phenyl-4,5,6,7-tetrafluorophthalimides known to be inhibitors of tumour necrosis factor-α (TNFα) production. Pharmacomodulation at the phthalimidic nitrogen led to the selection of two pharmacophoric fragments (2,4-lutidinyl and β-picolyl), allowing significant inhibition of TNFα production (compounds 12 and 17). Variation of the substituents linked to the homocycle of their phthalimide scaffold indicated that high (TNFα production) inhibitory potency could be achieved, notably by 5-fluoro, 4- or 5-nitro, 5-amino and especially tetrafluoro substitution. The most active compound, N-(pyridin-3-ylmethyl)-4,5,6,7-tetrafluorophthalimide (32) (84% inhibition at 10 μM), also produced an anti-oedematous effect in the PMA-induced mouse-ear swelling test. Although less active than dexamethasone, it exerted a marked reduction in ear thickness after oral administration (63% vs. 85% for dexamethasone at 0.2 mM kg-1) and remained efficient after topical application (46% vs. 96% for the dexamethasone). It also induced potent inhibition in the rat carrageenan foot oedema test with an ID50 (0.14 μM kg-1) comparable with that of N-(2,6-diisopropylphenyl)phthalimide (4) (0.15 μM kg-1).