6621-97-2

Upstream product

• 520-03-6 N-phenylphthalimide 
• 108-86-1 bromobenzene 
• 36149-35-6 3-anilino-3-phenyl-3H-isobenzofuran-1-one 
• 487-42-3 N-Phenylphthalisoimid 
• 71-43-2 benzene 
• 110474-85-6 2-(2-chloro-1-phenyl-vinyl)-benzoic acid anilide 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 24259-39-0 N-Phenylphthalisoimidium perchlorate 
• 18852-53-4 3-chloro-3-phenylphthalide 
• 62-53-3 aniline 
• 23450-18-2 2-benzyl-1-bromobenzene 
• 612-35-1 2-Benzylbenzoic acid 
• 15310-01-7 benodanil 

Downstream Products

• 79419-94-6 3-(1H-imidazol-1-yl)-2,3-diphenylisoindolin-1-one 
• 102242-28-4 3-benzyl-3-phenyl-3H-isobenzofuran-1-one 
• 132501-14-5 1,3-di-hydroxy-1,2,3-triphenylphtalimidine 
• 5004-45-5 4-phenyl-2H-phthalazin-1-one 
• 123217-56-1 2,3-diphenylisoindoline-1-thione 
• 5398-11-8 3-phenylphthalide 

Relevant academic research and scientific papers

Copper-catalyzed aerobic double functionalization of benzylic C(sp3)-H bonds for the synthesis of 3-hydroxyisoindolinones

A copper-catalyzed aerobic 3-hydroxyisoindolinone synthesis was developed via the benzylic double C(sp3)-H functionalization of 2-alkylbenzamides. In this reaction, molecular oxygen was used as both an oxidant for C(sp3)-H functionalization and an oxygen source. Our method can be extended to diverse benzylic C(sp3)-H bonds and shows excellent functional group tolerance. This journal is

Copper-catalysed synthesis of 3-hydroxyisoindolin-1-ones from benzylcyanide 2-iodobenzamides

An efficient one-pot two-step sequential reaction for the synthesis of biologically active 3-hydroxyisoindolin-1-one derivatives from 2-iodobenzamide derivatives and various substituted benzyl cyanides in the presence of CuCl and cesium carbonate in DMSO is reported. Furthermore, 3-hydroxyisoindolinone derivatives possessing bromo substituents were obtained from 2-iodobenzamide and 2-bromobenzyl cyanide substrates in two steps. Benzyl cyanide has been successfully used for the first time as a benzoyl synthon for the synthesis of 3-hydroxyisoindolin-1-ones. Interestingly, the mechanism of formation of 3-hydroxyisoindolin-1-ones is a novel pathway that involves carbon degradation followed by ring contraction.

Lithium–Bromide Exchange versus Nucleophilic Addition of Schiff's base: Unprecedented Tandem Cyclisation Pathways

By exploring lithium–bromide exchange reactivity of aromatic Schiff's bases with tert-butyllithium (tBuLi), we have revealed unprecedented competitive intermolecular and intramolecular cascade annulation pathways, leading to valuable compounds, such as iso-indolinones and N-substituted anthracene derivatives. A series of reaction parameters were probed, including solvent, stoichiometry, sterics and organolithium reagent choice, in order to understand the influences that limit such ring-closing pathways. With two viable reactivity options for the organolithium on the imine; namely, nucleophilic addition or lithium–bromide exchange, a surprising competitive nature was observed, where nucleophilic addition dominated, even under cryogenic conditions. Considering the most commonly used solvents for lithium–bromide exchange, tetrahydrofuran (THF) and diethyl ether (Et2O), contrasting reactivity outcomes were revealed with nucleophilic addition promoted in THF, while Et2O yielded almost double the conversion of cyclic products than in THF.

Eosin Y as a Redox Catalyst and Photosensitizer for Sequential Benzylic C?H Amination and Oxidation

A new synergistic multicatalytic activation mode of eosin Y has been discovered by exploiting the redox potential of its ground state and excited state. This catalytic strategy proves to be an enabling tool for visible-light-driven sequential benzylic C?H amination and oxidation of o-benzyl-N-methoxyl-benzamides when using Selectfluor as a hydrogen atom transfer (HAT) reagent and O2 as oxidant. Efficient synthesis of a range of diversely functionalized 3-hydroxyisoindolinones can thus be achieved with good yields and selectivity at mild reaction conditions. Preliminary mechanistic studies and DFT calculations suggest that eosin Y works as a redox catalyst and photosensitizer.

Preparation of 3-Hydroxyindolin-1-ones and o-Acylbenzamides. A Study of Ring-Chain Tautomerism

3-Hydroxyisoindolinones (ring form) as well as their chain tautomers, o-acylbenzamides, were prepared from the reactions of 3-benzalphthalide 1, 3-halophthalides 3, and o-acylbenzoic acids 6 or their esters 7 with amines 2, and those of phthalimides 4 wit

Reaction of N-Arylphthalisoimidium Perchlorates with Amines and Aromatic Hydrocarbons under Friedel-Crafts Conditions, a New and Convenient One-Step Method for the Synthesis of 2,3-Diaryl-3-hydroxyphthalimidines

N-Arylphthalisoimidium perchlorates (1a, b) react with primary amines via ring-opening to give N,N'-disubstituted phthalamides (3a-d).They react with aromatic hydrocarbons under Friedel-Crafts conditions to give 2,3-diaryl-3-hydroxyphthalimidines (a-i) while the reaction of 1a wtith phenylmagnesium bromide involved just deprotonation to the isoimide (9) followed by rearrangement to N-phenylphthalimide (8).