5388-42-1

Usage

Uses

Used in Organic Synthesis:
2,3-Dihydro-2-phenyl-1H-isoindol-1-oxo-isoindoline is used as a starting material or intermediate in organic synthesis for the creation of various biologically active compounds. Its distinctive structure allows for the development of novel chemical entities with potential therapeutic applications.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 2,3-Dihydro-2-phenyl-1H-isoindol-1-oxo-isoindoline serves as a key intermediate in the synthesis of drugs. Its unique properties contribute to the discovery and design of new pharmaceutical agents with improved efficacy and selectivity.
Used in Organic Electronics:
2,3-Dihydro-2-phenyl-1H-isoindol-1-oxo-isoindoline has potential applications in the field of organic electronics, where its electronic properties can be harnessed for the development of advanced materials and devices, such as organic light-emitting diodes (OLEDs) and organic solar cells.
Used as a Ligand in Coordination Chemistry:
In coordination chemistry, 2,3-Dihydro-2-phenyl-1H-isoindol-1-oxo-isoindoline can be utilized as a ligand to form coordination complexes with metal ions. This application can lead to the creation of new catalysts, sensors, and materials with tailored properties for various chemical and industrial processes.

InChI:InChI=1/C14H11NO/c16-14-13-9-5-4-6-11(13)10-15(14)12-7-2-1-3-8-12/h1-9H,10H2

Upstream product

• 87-41-2 2-benzofuran-1(3H)-one 
• 62-53-3 aniline 
• 1194-57-6 2-thiophthalide 
• 4741-68-8 3H-isobenzofuran-1-thione 
• 1531-78-8 o-(chloromethyl)benzoic acid ethyl ester 
• 2325-27-1 N-phenyltriphenyliminophosphorane 
• 643-79-8 o-phthalic dicarboxaldehyde 
• 622-37-7 Phenyl azide 
• 567-47-5 2-hydroxy-naphthalene-1-sulfonic acid 
• 201230-82-2 carbon monoxide 
• 6630-33-7 ortho-bromobenzaldehyde 
• 612-13-5 2-cyanobenzyl chloride 
• 1750-36-3 (E)-N-benzylidenebenzenamine 
• 50844-92-3 N-(2-bromobenzyl)benzenamine 

Downstream Products

• 520-03-6 N-phenylphthalimide 
• 4727-29-1 phthalanilic acid 
• 60025-40-3 2-(4-acetylphenyl)-2,3-dihydro-1H-isoindole-1-one 
• 1393881-91-8 N-(4-methylphenyl)-3-{[(4-methylphenyl)amino]methylidene}-2-phenyl-2,3-dihydro-1H-isoindol-1-imine hydrochloride 
• 1393881-92-9 3-(5,5-dimethyl-1,3-dioxan-2-yl)-2-phenyl-2,3-dihydro-1H-isoindol-1-one 
• 1393881-93-0 3-(diethoxymethyl)-2-phenyl-2,3-dihydro-1H-isoindol-1-one 
• 1393881-94-1 3-(ethoxymethylidene)-2-phenyl-2,3-dihydro-1H-isoindol-1-one 
• 1393881-95-2 3-ethyl-1-(phenylamino)-3,4-dihydro-1H-2-benzopyran-4-one 
• 1393881-96-3 3-butyl-1-(phenylamino)-3,4-dihydro-1H-2-benzopyran-4-one 
• 1393881-90-7 3-chloro-2-phenyl-2H-isoindole-1-carbaldehyde 
• 107456-50-8 (2-anilinomethyl-phenyl)-methanol 
• 89313-76-8 2-phenylisoindoline-1-thione 

Relevant academic research and scientific papers

Electroselective and Controlled Reduction of Cyclic Imides to Hydroxylactams and Lactams

An efficient and practical electrochemical method for selective reduction of cyclic imides has been developed using a simple undivided cell with carbon electrodes at room temperature. The reaction provides a useful strategy for the rapid synthesis of hydroxylactams and lactams in a controllable manner, which is tuned by electric current and reaction time, and exhibits broad substrate scope and high functional group tolerance even to reduction-sensitive moieties. Initial mechanistic studies suggest that the approach heavily relies on the utilization of amines (e.g., i-Pr2NH), which are able to generate α-aminoalkyl radicals. This protocol provides an efficient route for the cleavage of C-O bonds under mild conditions with high chemoselectivity.

Visible-Light-Induced Controlled Oxidation of N-Substituted 1,2,3,4-Tetrahydroisoquinolines for the Synthesis of 3,4-Dihydroisoquinolin-1(2H)-ones and Isoquinolin-1(2H)-ones

A visible light-rose bengal-TBHP mediated, controlled oxidation of N-substituted 1,2,3,4-tetrahydroisoquinolines is developed for the synthesis of 3,4-dihydroisoquinolin-1(2H)-ones and isoquinolin-1(2H)-ones. The present method feature's a broad substrate scope, good functional group tolerances, and the products were prepared in good to excellent yields. The developed methodology further demonstrated in the synthesis of isoindolo[2,1-b] isoquinolin-5(7H)-one (topoisomerase-I inhibitor). (Figure presented.).

Cobalt nanoclusters coated with N-doped carbon for chemoselective nitroarene hydrogenation and tandem reactions in water

The development of active and selective non-noble metal-based catalysts for the chemoselective reduction of nitro compounds in aquo media under mild conditions is an attractive research area. Herein, the synthesis of subnanometric and stable cobalt nanoclusters, covered by N-doped carbon layers as core-shell (Co@NC-800), for the chemoselective reduction of nitroarenes is reported. TheCo@NC-800catalyst was prepared by the pyrolysis of the Co(tpy)2complex impregnated on Vulcan carbon. In fact, the use of a molecular complex based on six N-Co bonds drives the formation of a well-defined and distributed cobalt core-shell nanocluster covered by N-doped carbon layers. In order to elucidate its nature, it has been fully characterized by using several advanced techniques. In addition, this as-prepared catalyst showed high activity, chemoselectivity and stability toward the reduction of nitro compounds with H2and under mild reaction conditions; water was used as a green solvent, improving the previous results based on cobalt catalysts. Moreover, theCo@NC-800catalyst is also active and selective for the one-pot synthesis of secondary aryl amines and isoindolinones through the reductive amination of nitroarenes. Finally, based on diffraction and spectroscopic studies, metallic cobalt nanoclusters with surface CoNxpatches have been proposed as the active phase in theCo@NC-800material.

Metal-Free Cascade Formation of Intermolecular C-N Bonds Accessing Substituted Isoindolinones under Cathodic Reduction

An electrochemical protocol for the construction of substituted isoindolinones via reduction/amidation of 2-carboxybenzaldehydes and amines has been realized. Under metal-free and external-reductant-free electrolytic conditions, the reaction achieves the cascade formation of intermolecular C-N bonds and provides a series of isoindolinones in moderate to good yields. The deuterium-labeling experiment proves that the hydrogen in the methylene of the product is mainly provided by H2O in the system.

Copper-promoted direct amidation of isoindolinone scaffolds by sodium persulfate

Isoindolinones are ubiquitous structural motifs in natural products and pharmaceuticals. Establishing an efficient method for structural modification of isoindolinones could significantly facilitate new drug development. Herein, we describe copper-promoted direct amidation of isoindolinone scaffolds mediated by sodium persulfate. The method exhibits mild reaction conditions and high site-selectivity, and enables the structural modification of the drug indobufen ester with various amides with yields of 49 to 98%. It is also gram-scalable. Additionally, the reaction mechanism appears to involve a radical and a carbocationic pathway.

One-pot method to construct isoindolinones and its application to the synthesis of DWP205109 and intermediate of Lenalidomide

Herein a practical and efficient system for concise synthesis of isoindolinones is described by using substituted methyl 2-(halomethyl)benzoates and substituted amines. Structurally various methyl 2-(halomethyl)benzoates and amines were transformed into isoindolinones 80–99% yield and purity in catalyst-free and solvent-free conditions. The method has a wide substrate scope. The synthetic utility of the one-pot reaction was demonstrated by the concise syntheses of Lenalidomide intermediate and DWP205190.

Homogeneous cobalt-catalyzed deoxygenative hydrogenation of amides to amines

The first general and efficient cobalt-catalyzed deoxygenative hydrogenation of amides to amines is presented. The optimal catalytic system based on a combination of [Co(NTf2)2] and (p-anisyl)triphos (L3) in the presence of [Me3SiOTf] as acidic co-catalyst facilitates the direct hydrogenation of a broad range of amides to the corresponding amines under mild conditions. A set of control experiments indicate that, after the initial reduction of the amide carboxylic group to the well-known hemiaminal intermediate, the reaction mainly proceeds through C-O bond cleavage though other pathways might be also involved to a minor extent. This journal is

Investigation towards the reductive amination of levulinic acid by B(C6F5)3/hydrosilane system

The selective transformation of the renewable biomass resources into the highly value-added platform chemicals is essentially important for sustainable chemistry. Here we report a simple and highly efficient strategy for the synthesis of N-heterocyclic co

Reductive amination of levulinic acid to N-substituted pyrrolidones over RuCl3 metal ion anchored in ionic liquid immobilized on graphene oxide

Reductive amination of biomass derived Levulinic acid (LA) for the synthesis of N-substituted pyrrolidones is one of the highly attractive routes for biomass valorization. The supported homogeneous metal precursor into the solid surface is an important context in the field of catalysis because these types of catalysts provide the heterogeneous nature and meet the needs of recyclability. Herein, we have reported a synthesis of catalyst with ruthenium ion supported on ionic liquid immobilized into graphene oxide (Ru?GOIL) and its application for reductive amination reaction. Synthesized catalyst is characterized using different analytical techniques such as FT-IR, XRD, XPS, TGA, FEG-SEM, TEM and EXAFS analysis. The prepared Ru?GOIL found to be highly effective for reductive amination of LA and under these optimized conditions various N-substituted pyrrolidones derivatives were synthesized in excellent yield (78–93%). Ru?GOIL catalyst demonstrated great catalytic performance for reductive amination reaction of LA giving good turnover frequency (TOF = 62 h?1) value in comparison with other catalysts. The Ru?GOIL catalyst was recycled for six reaction runs with slight drop-in activity after 4th cycle. Practical applicability of the developed catalyst was successfully demonstrated by direct transformation of biomass waste (rice husk and wheat straw) derived LA to N-substituted pyrrolidones.

One-pot synthesis of pyrrolidones from levulinic acid and amines/nitroarenes/nitriles over the Ir-PVP catalyst

The synthesis of pyrrolidones via reductive amination of levulinic acid with aniline was examined over polypyrrolidone-stabilized metal nanoparticle catalysts. Among them, Ir metal was the most effective and applicable for the reductive amination of levulinic acid with nitroarenes/nitriles. Importantly, this catalyst was used for the one-pot synthesis of the anti-inflammatory drug indoprofen from 2-formylbenzoic acid and 2-(4-nitrophenyl)propanoic acid.