4778-82-9

Usage

Chemical Class

Isoindolones

Function

Dopamine agonist

Medical Uses

Treatment of Parkinson's disease and restless legs syndrome

Mechanism of Action

Stimulates dopamine receptors in the brain to improve motor function and reduce symptoms such as tremors, stiffness, and slowness of movement

Available Forms

Tablets, extended-release tablets, and transdermal patch

Effectiveness

Effective in managing symptoms of Parkinson's disease and restless legs syndrome

Patient Toleration

Well-tolerated by most patients, making it a valuable treatment option

Upstream product

• 783-08-4 [4-(benzylideneamino)phenyl]methanol 
• 74-88-4 methyl iodide 
• 201230-82-2 carbon monoxide 
• 40400-13-3 2-Iodobenzyl bromide 
• 104-94-9 4-methoxy-aniline 
• 6630-33-7 ortho-bromobenzaldehyde 
• 1234560-03-2 C₂₂H₁₈BrNO₄ 
• 1374222-86-2 dimethyl 2-(4-methoxyphenyl)-3-oxoisoindolin-1-ylphosphonate 
• 119-67-5 o-carboxybenzaldehyde 
• 87-41-2 2-benzofuran-1(3H)-one 
• 2417-73-4 methyl 2-bromomethylbenzoate 
• 89-71-4 2-Methyl-benzoic acid methyl ester 
• 73357-44-5 2-(4-methoxyphenyl)-2,3-dihydro-1H-isoindole 
• 480-91-1 oxisoindole 

Downstream Products

• 73357-39-8 2-(4-methoxyphenyl)-2H-isoindole 
• 89313-77-9 2-(p-anisyl)isoindoline-1-thione 
• 141663-78-7 12-(4-Methoxy-phenyl)-11,11-dimethyl-9-thia-12-aza-tricyclo[6.3.1.0^2,7]dodeca-2,4,6-triene 
• 141663-77-6 12-(4-Methoxy-phenyl)-10,10,11,11-tetramethyl-9-thia-12-aza-tricyclo[6.3.1.0^2,7]dodeca-2,4,6-triene 
• 141663-79-8 (1R,8R,11S)-12-(4-Methoxy-phenyl)-11-methyl-9-thia-12-aza-tricyclo[6.3.1.0^2,7]dodeca-2,4,6-triene-11-carbonitrile 
• 141663-79-8 (1R,8R,11R)-12-(4-Methoxy-phenyl)-11-methyl-9-thia-12-aza-tricyclo[6.3.1.0^2,7]dodeca-2,4,6-triene-11-carbonitrile 
• 93273-30-4 C₂₇H₂₄N₂O₃S 

Relevant academic research and scientific papers

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.

BF3·Et2O as a metal-free catalyst for direct reductive amination of aldehydes with amines using formic acid as a reductant

A versatile metal- and base-free direct reductive amination of aldehydes with amines using formic acid as a reductant under the catalysis of inexpensive BF3·Et2O has been developed. A wide range of primary and secondary amines and diversely substituted aldehydes are compatible with this transformation, allowing facile access to various secondary and tertiary amines in high yields with wide functional group tolerance. Moreover, the method is convenient for the late-stage functionalization of bioactive compounds and preparation of commercialized drug molecules and biologically relevant N-heterocycles. The procedure has the advantages of simple operation and workup and easy scale-up, and does not require dry conditions, an inert atmosphere or a water scavenger. Mechanistic studies reveal the involvement of imine activation by BF3and hydride transfer from formic acid.

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.

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.

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.

Synthetic method of isoindolinone compound

The invention belongs to the field of chemical synthesis, and particularly relates to a synthesis method of an isoindolinone compound. The isoindolinone compound is represented by formula (I), in which R, R1 and R2 are used for representing any substituent groups. According to the synthetic method of the isoindolinone compound, a new process for solvent-free synthesis of the isoindolinone compoundis developed; no solvent is used, so that the separation and purification process of the product is easier to carry out, the green production of fine chemicals is effectively realized, the operationis simple, the reaction time is obviously shortened, the production efficiency of the product is increased, the quality and yield are improved, the yield can reach 81%-99%, and the purity can reach 96%-99%.

Formic acid as a hydrogen source for the iridium-catalyzed reductive amination of levulinic acid and 2-formylbenzoic acid

The aqueous phase catalytic reductive amination of levulinic acid (LA) into pyrrolidones and 2-formylbenzoic acid into N-arylisoindolines is reported. The catalytic reaction involves an iridium catalyst bearing an electron-rich dipyridylamine ligand and u

Ruthenium(ii)-catalysed selective C(sp2)-H bond benzoxylation of biologically appealing: N -arylisoindolinones

Site- and regio-selective aromatic C-H bond benzoxylations were found to take place using biologically appealing N-arylisoindolinones under ruthenium(ii) catalysis in the presence of (hetero)aromatic carboxylic acid derivatives as coupling partners. Besides the presence of two potential C(sp2)-H sites available for functionalization in the substrates, exclusive ortho selectivity was achieved in the phenyl ring attached to the nitrogen atom. Notably, the reactions occurred in a selective manner as only mono-functionalized products were formed and they tolerated a large number of functional chemical groups. The ability of the cyclic tertiary amide within the isoindolinone skeleton to act as a weak directing group in order to accommodate six-membered ring ruthenacycle intermediates appears to be the key to reach such high levels of selectivity. In contrast, the more sterically demanding cyclic imides were unreactive under identical reaction conditions.

Site-Selective Ruthenium-Catalyzed C-H Bond Arylations with Boronic Acids: Exploiting Isoindolinones as a Weak Directing Group

Biologically relevant N-arylisoindolinones efficiently underwent arylation reactions under ruthenium catalysis via C-H bond functionalization. The reactions exclusively led to monoarylated products, and only ortho selectivity was observed in the aromatic ring connected to the nitrogen atom. Interestingly, no C-H bond functionalization was observed in the other benzene ring in the ortho position with respect to the carbonyl group. This ruthenium-catalyzed reaction displayed a high functional group tolerance, and it employed readily available and benchmark stable boronic acid and potassium aryltrifluoroborate derivatives as coupling partners. An appealing late-stage functionalization of indoprofen applying this methodology is showcased.