92552-45-9

Upstream product

• 1749-19-5 phenyl(1-phenylethylidene)amine 
• 1234560-05-4 C₂₂H₁₈BrNO₃ 
• 50604-01-8 ethyl-benzoic acid methyl ester 
• 16281-95-1 2-(1-Bromethyl)-benzoesaeuremethylester 
• 62-53-3 aniline 
• 1416618-81-9 C₁₅H₁₃NO₂ 
• 6091-76-5 3-methyl-1-oxoisoindoline 
• 76118-05-3 2-ethylbenzoyl chloride 
• 56776-51-3 2-ethyl-N-phenylbenzamide 
• 26040-23-3 N-phenyl-2-acetylbenzamide 
• 7647-01-0 hydrogenchloride 
• 71-43-2 benzene 

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.

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%.

Generation of Phosphoranyl Radicals via Photoredox Catalysis Enables Voltage-Independent Activation of Strong C-O Bonds

Despite the prevalence of alcohols and carboxylic acids as functional groups in organic molecules and the potential to serve as radical precursors, C-O bonds remain difficult to activate. We report a synthetic strategy for direct access to both alkyl and acyl radicals from these ubiquitous functional groups via photoredox catalysis. This method exploits the unique reactivity of phosphoranyl radicals, generated from a polar/SET crossover between a phosphine radical cation and an oxygen-centered nucleophile. We show the desired reactivity in the reduction of benzylic alcohols to the corresponding benzyl radicals with terminal H atom trapping to afford the deoxygenated products. Using the same method, we demonstrate access to synthetically versatile acyl radicals, which enables the reduction of aromatic and aliphatic carboxylic acids to the corresponding aldehydes with exceptional chemoselectivity. This protocol also transforms carboxylic acids to heterocycles and cyclic ketones via intramolecular acyl radical cyclizations to forge C-O, C-N, and C-C bonds in a single step.

Phthalimidine synthesis via the direct condensation between phthalide and primary amine in the presence of catalytic amount of InCl3

Background: We previously reported the 1:1 condensation reaction between ophthalaldehyde and primary amine in the presence of 1,2,3-1H-benzotriazole and 2-mercaptoethanol as dual synthetic auxiliaries to provide phthalimidines (2,3-dihydroisoindol-1-ones) under mild reaction conditions in good isolated yields. However, this reaction was found to proceed via dissymmetrization of equi-oxidation stage functionalities (carbonyl groups herein), which would give rise to regioisomer(s) whenever the orientation of substituents in the target molecule phthalimidine was dissymmetrical. In order to overcome such defects, we focused on phthalide, which possessed identical electronic structure with that of target molecule phthalimidine. Thus, the condensation between a phthalide derivative and a primary amine would eliminate a water molecule, but does not accompany with any kind of redox paths. Therefore, dissymmetrical trends possessed by the phthalide derivative should transfer directly to the resulting phthalimidine, and as a result the formation of possible regioisomer(s) can completely be prevented. This strategy has existed as the oldest method of phthalimidine synthesis, however, Lewis acid catalysts utilized in the past were not appropriate to extend its scope. In this report, we demonstrate an improved method of phthalimidine synthesis along this line using InCl3 as a catalyst, which would allow the synthesis of this class to accommodate with the contemporary standard of organic syntheses. Method: In general, aniline (2.0 mmol, used at once as reagent and solvent) was added to the flask containing phthalide (1.0 mmol) and InCl3 (an appropriate amount) under Ar atmosphere over Ca. 3 min with stirring, and the whole mixture was heated at gentle reflux for an appropriate period. After usual work-up, crude products were purified by column chromatography on silica gel. Isolated components were ascertained by 1H NMR spectral comparison with the authentic samples prepared by our former methods. Results: Optimization of the reaction condition was explored using phthalide and aniline. Thus, decrement of yields occurred whenever amounts of InCl3 catalyst were reduced, however, longer reaction periods improved isolated yields every time. Even in the use of 1 mol% of InCl3 catalyst, reaction would complete within a few days. As a result, the direct condensation between phthalide and aniline with the use of a truly catalytic amount of Lewis acid catalyst was made possible for the first time in the history of phthalimidine syntheses. Extension of this strategy to some primary amines other than aniline was successful, too. Based on experimental results, our plausible mechanism was proposed, in which the reaction commenced by nucleophilic attack of an amino group towards 3-position of oxygen-chelated phthalide. Conclusion: We succeeded in the direct condensation reaction between phthalide and primary amine in the presence of a catalytic amount of Lewis acid catalyst, InCl3, for the first time. Although successful examples have thus far been limited to some combination that affords clear reaction mixtures (except for the catalyst) under high-temperature, solvent-free heating, we believe that we have attained a tacit basis to prepare a variety of phthalimidine derivatives possessing a variety of substituent patterns.

Copper-Catalyzed sp3 C-H Aminative Cyclization of 2-Alkyl-N-arylbenzamides: An Approach for the Synthesis of N-Aryl-isoindolinones

The synthesis of isoindolinones via copper-catalyzed sp3 C-H functionalization of 2-alkyl-N-substituted benzamides is described. This process does not require the preparation of halogenated substitutes, expensive transition metals, or toxic Sn or CO gas. This method provides an efficient approach to generate various functionalized isoindolinones.

Highly efficient and versatile synthesis of lactams and N -heterocycles via Al(OTf)3-catalyzed cascade cyclization and ionic hydrogenation reactions

The discovery and development of an efficient and versatile method for the synthesis of N-substituted lactams is described. Pyrrolindinones, piperidones, and structurally related heterocycles were formed by Al(OTf)3- catalyzed cascade cyclizati

Synthesis of N -arylisoindolin-1-ones via pd-catalyzed intramolecular decarbonylative coupling of N -(2-bromobenzyl)oxanilic acid phenyl esters

Ethyl and phenyl oxanilates were readily prepared from N-(2-bromobenzyl) anilines and oxalyl chloride monoethyl and monophenyl esters, respectively. It was found that the ethyl oxanilate survived in the presence of K 2CO3 in DMA at 120°C and underwent an intramolecular direct arylation using Pd(OAc)2-dppf, furnishing the 5,6-dihydrophenanthridine derivative. In contrast, the corresponding phenyl oxanilates decomposed upon exposure to K2CO3 in DMA at 120 C and were transformed into N-arylisoindolin-1-ones via Pd(OAc) 2-dppf-catalyzed intramolecular decarbonylative coupling. Except for the 4-methoxy-substituted oxanilic acid phenyl ester, other phenyl oxanilates possessing electron-withdrawing (NO2, Cl) and weak electron-donating (Me) substituents provided the N-arylisoindolin-1-ones in 43-80% yields.

Novel chemoselective desulfurization of γ-phenylthio-substituted aromatic lactams: Application to the synthesis of isoindolobenzazepine alkaloid, lennoxamine

Treatment of a variety of γ-phenylthio-substituted aromatic lactams with lithium aluminum hydride in the presence of cuprous iodide led to novel chemoselective desulfurization reactions to afford the corresponding substituted aromatic lactams without givi