92855-70-4

Upstream product

• 19438-61-0 4-methylphthalic anhydride 
• 100-46-9 benzylamine 
• 60956-23-2 3,4-dibromotoluene 
• 13939-06-5 molybdenum hexacarbonyl 
• 1631-26-1 1-benzyl-1H-pyrrole-2,5-dione 
• 107-86-8 3,3-dimethyl acrylaldehyde 

Downstream Products

• 1150647-56-5 2-benzyl-1,1,3,3-tetraethyl-5-methylisoindoline 
• 1443427-29-9 N-benzyl-1,1,3,3,5-pentamethylisoindoline 
• 111293-91-5 6-methyl-3-phenylisoquinoline 
• 1159003-64-1 7-methyl-3-phenylisoquinoline 
• 97754-25-1 2-benzyl-5-methylisoindoline 

Relevant academic research and scientific papers

Organocatalyzed Synthesis of Highly Functionalized Phthalimides via Diels-Alder Reaction Employing Two Dienophiles

An efficient and facile protocol for the synthesis of biologically and pharmaceutically important phthalimides is developed by l-proline-catalyzed reaction between two dienophiles of α,β-unsaturated aldehydes and maleimides. The reaction involves an efficient benzannulation that proceeds via a formal [4 + 2] cycloaddition of azadiene intermediates generated in situ from enals and N-substituted maleimides. This protocol provides a variety of functionalized phthalimide derivatives, including a potent COX-2 enzyme inhibitor.

Alkoxide-Catalyzed Hydrosilylation of Cyclic Imides to Isoquinolines via Tandem Reduction and Rearrangement

An alkoxide-catalyzed hydrosilylation of cyclic imides to isoquinolines was realized via tandem reduction and rearrangement. Using TMSOK as the catalyst and (EtO)2MeSiH as the reductant, a series of cyclic imides containing different functional groups were reduced to the corresponding 3-aryl isoquinolines in moderate to good yields. The scenario of the reaction pathway was supposed to involve the reduction of imides to ω-hydroxylactams, which underwent rearrangement in the presence of a base catalyst, and then the carbonyl reduction, followed by siloxy elimination.

Tri(pentaflurophenyl)borane-catalyzed reduction of cyclic imides with hydrosilanes: Synthesis of pyrrolidines

B(C6F5)3-catalyzed hydrosilylation of cyclic imides afforded an efficient synthetic method of pyrrolidines. In the presence of 5 mol% B(C6F5)3, various aromatic, aliphatic and polycyclic imides were smoothly reduced by PhSiH3 to generate the corresponding pyrrolidines in high yields. The reaction profiles monitored by 1H NMR spectroscopy disclosed the reduction process of cyclic imides and the effect of difference structure of the hydrosilanes on the hydrosilylation.

An efficient synthesis of N-substituted phthalimides using SiO2-tpy-Nb as heterogeneous and reusable catalyst

A novel and efficient heterogeneous catalyst SiO2-tpy-Nb was developed, and its application in the preparation of N-substituted phthalimides from o-phthalic acids or anhydrides with amines provides the desired products in good to excellent yields. The catalyst was stable and recoverable for eight consecutive cycles without a significant loss in its activity. Furthermore, the catalyst is applicable in continuous flow which indicates its potential utilization in industrialization.

Palladium-catalyzed carbonylative synthesis of phthalimides from 1,2-dibromoarenes with molybdenum hexacarbonyl as carbon monoxide source

We describe here a convenient and mild, carbon monoxide gas-free palladium-catalyzed procedure to obtain N-substituted phthalimides with molybdenum hexacarbonyl as carbon monoxide precursor. These conditions tolerate a number of functional groups on the benzene ring as well as a number of amines and give the corresponding phthalimides in good to excellent yields. Copyright

Approaches to the synthesis of a water-soluble carboxy nitroxide

The robust and diversely useful isoindoline nitroxide, 5-carboxy-1,1,3,3- tetramethylisoindolin-2-yloxyl (1; CTMIO), has previously been synthesised in low-to-moderate yields from phthalic anhydride (3). Recent interest in its biological potential as a potent antioxidant and in other areas has seen an increased demand for its production. Herein, three new synthetic routes to CTMIO are presented and their efficiencies assessed. Two routes, via the nitrile 9 and the formyl compound 11, derive from 5-bromo-1,1,3,3-tetramethylisoindoline (6). The third approach starts from the readily accessible starting material, 4-methylphthalic anhydride (12), and proceeds by a methylarene oxidation with potassium permanganate. The three new approaches yield CTMIO in comparable overall yields (16-18 %); however, the synthetic efficiency is most improved when employing the nitrile intermediate 9. Copyright

ANTIOXIDANT COMPOUNDS AND METHODS OF THEIR USE

The invention relates to antioxidant substituted isoindoline nitroxide compounds and their use in methods of treating or preventing diseases or disorders related to oxidative stress, methods of reducing oxidative stress and methods of protecting a subject from oxidative stress upon exposure to ionising radiation. Pharmaceutical compositions comprising the antioxidant compounds are also described.

ANTIOXIDANT COMPOUNDS AND METHODS OF THEIR USE

The invention relates to antioxidant substituted isoindoline nitroxide compounds and their use in methods of treating or preventing diseases or disorders related to oxidative stress, methods of reducing oxidative stress and methods of protecting a subject from oxidative stress upon exposure to ionising radiation. Pharmaceutical compositions comprising the antioxidant compounds are also described.

The synthesis of novel isoindoline nitroxides bearing water-solubilising functionality

A range of novel tetramethyl- and tetraethylisoindoline nitroxides, possessing aryl-linked carboxylic acids, amines, alcohols and phosphonic acids were prepared. Notably, the chemistry established for the aromatic dibromination of the tetramethylisoindoli