34493-83-9

Upstream product

• 201230-82-2 carbon monoxide 
• 3647-71-0 N-benzyl-2-phenylethylamine 
• 89-71-4 2-Methyl-benzoic acid methyl ester 
• 1074-82-4 potassium phtalimide 
• 103-63-9 1-phenyl-2-bromoethane 
• 7501-05-5 N-(2-phenylethyl)phthalimide 
• 23069-99-0 N-(2-phenylethyl)formamide 
• 643-79-8 o-phthalic dicarboxaldehyde 
• 2417-73-4 methyl 2-bromomethylbenzoate 
• 64-04-0 phenethylamine 
• 97754-27-3 2-phenethyl-2,3-dihydro-1H-isoindole 
• 91-13-4 α,α'-dibromo-o-xylene 
• 119-67-5 o-carboxybenzaldehyde 
• 85-44-9 phthalic anhydride 

Downstream Products

• 7501-05-5 N-(2-phenylethyl)phthalimide 

Relevant academic research and scientific papers

Complete structural and spectral assignment of oxoisoaporphines by HMQC and HMBC experiments

The oxoisoaporphines 2,3-dihydro-7H-dibenzo[de,h]quinolin-7-one, 2,3-dihydro-5-methoxy-7H-dibenzo [de,h] quinolin-7-one, 5-methoxy-6-hydroxy-2,3-dihydro-7H-dibenzo[de,h]quinolin-7-one, 5,6-dimethoxy-2,3-dihydro-7H-dibenzo[de,h]quinolin-7-one and 5,6-methy

Tunable System for Electrochemical Reduction of Ketones and Phthalimides

Herein, we report an efficient, tunable system for electrochemical reduction of ketones and phthalimides at room temperature without the need for stoichiometric external reductants. By utilizing NaN3 as the electrolyte and graphite felt as both the cathode and the anode, we were able to selectively reduce the carbonyl groups of the substrates to alcohols, pinacols, or methylene groups by judiciously choosing the solvent and an acidic additive. The reaction conditions were compatible with a diverse array of functional groups, and phthalimides could undergo one-pot reductive cyclization to afford products with indolizidine scaffolds. Mechanistic studies showed that the reactions involved electron, proton, and hydrogen atom transfers. Importantly, an N3/HN3 cycle operated as a hydrogen atom shuttle, which was critical for reduction of the carbonyl groups to methylene groups.

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.

Synthesis of tertiary amines by direct Br?nsted acid catalyzed reductive amination

Tertiary amines are ubiquitous and valuable compounds in synthetic chemistry, with a wide range of applications in organocatalysis, organometallic complexes, biological processes and pharmaceutical chemistry. One of the most frequently used pathways to synthesize tertiary amines is the reductive amination reaction of carbonyl compounds. Despite developments of numerous new reductive amination methods in the past few decades, this reaction generally requires non-atom-economic processes with harsh conditions and toxic transition-metal catalysts. Herein, we report simple yet practical protocols using triflic acid as a catalyst to efficiently promote the direct reductive amination reactions of carbonyl compounds on a broad range of substrates. Applications of this new method to generate valuable heterocyclic frameworks and polyamines are also included.

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%.

Isoindolinone Synthesis: Selective Dioxane-Mediated Aerobic Oxidation of Isoindolines

N-Alkyl and N-aryl-isoindolinones were prepared by a dioxane-mediated oxidation of isoindoline precursors. The transformation exhibits unique chemoselectivity for isoindonlines. A chiral tertiary (3°)-benzylic position was not racemized during oxidation, and methyl indoprofen was prepared by late stage oxidation. Mechanistic studies suggest a selective H atom transfer, which avoids many known oxidation (by-)products of isoindolinones.

Hantzsch ester triggered metal-free cascade approach to isoindolinones

Disclosed herein is an expedient synthesis of biologically important isoindolinone derivatives from reactions of 2-formylbenzoic acids with various amines. This method operates via a deliberately designed catalyst-free tandem reductive amination/cyclization cascade event triggered by a transfer hydrogenation process with easily available Hantzsch ester as the organic hydride source. The ease of operation, mild reaction conditions, facile accessibility of the starting materials, and easy scalability of the current method distinguish it from the other precedent protocols, thus enable it a practical approach to the syntheses of valuable isoindolinone-incorporated drugs.

Application of the mild-condition phthalimidine synthesis with use of 1,2,3-1h-benzotriazole and 2-mercaptoethanol as dual synthetic auxiliaries. Effective synthesis of phthalimidines possessing a variety of substituents at 2-position

The mild-condition phthalimidine synthesis based on Mannich type 1:1 condensation reaction between o-phthalaldehyde with a variety of primary amines in the presence of excess 2-mercaptoethanol and 1,2,3-1H-benzotriazole as "dual synthetic auxiliaries" in MeCN for 13 h at room temperature afford 2-substituted phthalimidines (2,3-dihydroisoindol-1-one) in fair to good isolated yields.

Direct one-pot cobalt(II) phthalocyanine catalyzed synthesis of N-substituted isoindolinones

A direct one-pot synthetic approach is described wherein cobalt(II) phthalocyanine (CoPc) catalyzed reductive amination of 2-carboxybenzaldehyde, followed by intramolecular amidation afforded N-substituted isoindolinones. The method used diphenylsilane as reducing agent in ethanol. High chemoselectivity with excellent yield was obtained in most of the studied substrates.

Synthesis of substituted amines and isoindolinones: Catalytic reductive amination using abundantly available AlCl3/PMHS

AlCl3 has been employed for highly chemoselective reductive amination of carbonyl compounds in ethanol using polymethylhydrosiloxane as an inexpensive, stable and safe reducing agent without an inert atmosphere. A large range of functional groups such as nitro, carboxylic acid, acetyl, nitrile, halogen, methoxy, alkene and heterocycles were well tolerated. AlCl3 also catalyzed tandem amination-amidation of 2-carboxybenzaldehyde with different amines to afford N-substituted isoindolinones. The catalyst can be recycled at least three times without any significant effect on activity and selectivity.