16082-71-6

Upstream product

• 85-44-9 phthalic anhydride 
• 108-42-9 3-chloro-aniline 
• 109949-63-5 2-(3-chlorophenyl)-2,3-dihydro-1H-isoindole 
• 670-54-2 ethenetetracarbonitrile 
• 13208-31-6 N_.N'-Di-(m-chlor-phenyl)-harnstoff 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 88-67-5 2-Iodobenzoic acid 
• 201230-82-2 carbon monoxide 
• 524-38-9 N-hydroxyphthalimide 
• 1864-94-4 phenyl formate 
• 197141-50-7 N-(3-chlorophenyl)-o-iodobenzamide 
• 3481-09-2 N-chlorophthalimide 
• 108-90-7 chlorobenzene 
• 136918-14-4 phthalimide 

Downstream Products

• 79419-89-9 2-(3-Chloro-phenyl)-3-hydroxy-3-phenyl-2,3-dihydro-isoindol-1-one 
• 37896-09-6 2-(3-chloro-phenyl)-3-hydroxy-2,3-dihydro-isoindol-1-one 
• 108474-71-1 2-(2-amino-4-chloro-benzoyl)-benzoic acid 

Relevant academic research and scientific papers

Imidazole-promoted synthesis of n-substituted phthalimide from N,N'-disubstituted ureas in solventless conditions

A series of N-substituted phthalimides was synthesized by a thermal reaction between N,N0-disubstituted ureas and phthalic acid catalyzed by imidazole in solventless conditions. The products have been obtained in moderate to good yields (53-92%). Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications1 to view the free supplemental file. Copyright Taylor & Francis Group, LLC.

Synthesis and hypolipidemic activity of N-substituted phthalimides. Part V

A series of N-aryl- or N-(1,2,4-triazol-yl)-phthalimides (4a-4i) have been synthesized starting from phthalic anhydride (1) and an appropriate amine (2a-2i). All compounds presented hypolipidemic activity, but compound 4d proved to be the most active and reduced plasma cholesterol and triglyceride levels in Swiss white mice significantly.

Visible-Light-Induced Metal-/Photocatalyst-Free C-H Bond Imidation of Arenes

In this study, a visible-light-induced intermolecular C-H bond imidation of arenes was achieved at ambient condition. By using simple phthalimide with (diacetoxyiodo)benzene and molecular iodine, direct metal-/photocatalyst-free C-N bond formation was achieved. The imidation protocol was designed by using time-dependent density functional theory calculations and experimentally demonstrated for 28 substrates with as high as 96% yield. Mechanistic studies indicated that radical-mediated aromatic substitution occurred via photolysis of N-iodophthalimide under visible-light irradiation.

Br?nsted acid mediated intramolecular cyclopropane ring expansion/[4 + 2]-cycloaddition

A cascade reaction of 3-hydroxy-2-phenylisoindolin-1-one and cyclopropyl ketone has been developed via a Br?nsted acid-promoted ring-opening/intramolecular cross-cycloaddition/[4 + 2]-cycloaddition process. The developed methodology provides straightforward access to pentacyclic isoindolin-1-one derivatives under simple reaction conditions.

Carbonylative synthesis of phthalimides and benzoxazinones by using phenyl formate as a carbon monoxide source

A simple and efficient palladium-catalyzed carbonylative cyclization of N-substituted 2-iodobenzamides and 2-iodoanilides was investigated for the synthesis of phthalimides and benzoxazinones, respectively, by using phenyl formate as a CO source. The present catalytic protocol circumvents the use of an expensive phosphine ligand as well as solvent in the case of the phthalimide synthesis. Moreover, mild reaction conditions and a tolerance of various functional groups enhance the general applicability of this method.

A phthalimidation protocol that follows protein defined parameters

This work outlines the first phthalimidation protocol suitable for protein labeling and performed in aqueous media at room temperature and neutral pH with no catalyst or co-reagent required. The methodology is suitable for a range of amines and its efficiency was determined with chemoselective and site-selective protein labeling. This journal is

Nitrogen-centered radical-mediated C-H imidation of arenes and heteroarenes via visible light induced photocatalysis

The C-H imidation of arenes and heteroarenes has been achieved via visible light induced photocatalysis. In the presence of an iridium(iii) photoredox catalyst, the reaction of aromatic substrates with N-chlorophthalimide furnishes the N-aryl products at room temperature through a nitrogen-centered radical mediated aromatic substitution.

Synthesis and antiseizure evaluation of isoindoline-1,3-dione derivatives in mice

Epilepsy is the most common serious chronic noninfective neurological condition in the world. Despite the presence of various antiepileptic drugs in the market for epileptic patients, the necessity for development and discovery of novel antiepileptic drugs is felt. In fact, only 60-70 % of patients respond to the current drugs, and a high incidence of adverse effects is also observed. In the present study, a new series of phthalimide derivatives (compounds 3a-3m) were synthesized through the reaction of phthalic anhydride and various derivatives of aniline in toluene solvent (Reflux, 24 h). Antiepileptic activity of synthesized compounds (3a-3m) was investigated using two experimental models namely, maximal electroshock (MES) and pentylenetetrazole (PTZ), and the obtained results were compared with diazepam as reference drug. Neurotoxicity of compounds was also evaluated using rotarod model. Compound 3m with para methoxy substituent exhibited the anticonvulsant activity at 15.1 ± 1.53 (12.23-17.96) mg/kg dose in MES model compared to other derivatives. Unfortunately, none of the tested compounds rendered acceptable protection in subcutaneous PTZ model.

Immobilized palladium metal containing ionic liquid catalyzed one step synthesis of isoindole-1,3-diones by carbonylative cyclization reaction

Immobilized palladium metal containing ionic liquid (ImmPd-IL) catalyzed carbonylative cyclization reaction of 2-iodobenzoic acid and primary amine provided N-substituted isoindole-1,3-dione derivatives in good to excellent yield. The influence of various reaction parameters including the effect of base, solvent, temperature, time and CO pressure on carbonylative cyclization reaction using ImmPd-IL catalyst was investigated. Using optimized reaction parameters different aromatic, aliphatic and heterocyclic N-substituted isoindole-1,3-dione derivatives were synthesized from corresponding aryl amines. The developed protocol is heterogeneous, phosphine free and requires attainable reaction conditions like atmospheric CO pressure and lesser reaction time. The scope of the developed protocol was also extended for the synthesis of N-substituted isoindole-1,3-diones from methyl-2-iodobenoate and 1,2-diiodo benzene. The ImmPd-IL catalyst was recyclable up to four consecutive cycles and recycled catalyst was characterized by XPS analysis.

Sterically controlled, palladium-catalyzed intermolecular amination of arenes

We report the Pd-catalyzed amination of arenes to form N-aryl phthalimides with regioselectivity controlled predominantly by steric effects. Mono-, di-, and trisubstituted arenes lacking a directing group undergo amination reactions with moderate to high yields and high regioselectivities from sequential addition of PhI(OAc)2 as an oxidant in the presence of Pd(OAc) 2 as catalyst. This sterically derived selectivity contrasts that for analogous arene acetoxylation.