17416-58-9

Upstream product

• 7501-05-5 N-(2-phenylethyl)phthalimide 
• 1074-82-4 potassium phtalimide 
• 103-63-9 1-phenyl-2-bromoethane 
• 91-13-4 α,α'-dibromo-o-xylene 
• 97754-27-3 2-phenethyl-2,3-dihydro-1H-isoindole 
• 64-04-0 phenethylamine 
• 85-44-9 phthalic anhydride 

Downstream Products

• 132868-78-1 2,3-Dihydro-3-oxo-2-(2-phenylethyl)-1H-isoindole-1-acetic Acid 
• 7501-05-5 N-(2-phenylethyl)phthalimide 
• 905772-52-3 C₂₆H₂₄N₂O 
• 942833-90-1 C₂₅H₂₂N₂O 
• 905775-00-0 C₂₅H₂₂N₂O 

Relevant academic research and scientific papers

1H and 13C NMR spectral assignments and X-ray crystallography of 4,5,8,12b-TETrahydro-isoindolo[1,2-a]isoquinoline and derivatives

12b-Hydroxy-5,6,8,12b-tetrahydroisoindolo[1,2-a]isoquinolin-8-one (4), 5,6,8,12b-tetrahydroisoindolo[1,2-a]isoquinoline (5) and 12b-hydroxy-5,6,8,12b- tetrahydroisoindolo[1,2-a]isoquinoline (6) were obtained by reduction of 4,5,8,12b-tetrahydroisoindolo[1

An Oxidation Study of Phthalimide-Derived Hydroxylactams

A systematic study of the oxidation of 3-hydroxy-2-substituted isoindolin-1-ones (hy-droxylactams) and their conversion to the corresponding phthalimides was undertaken using three oxidants. Of special interest was the introduction of nickel peroxide (NiO2 ) as an oxidation system for hydroxylactams and comparison of its performance with the commonly used pyridinium chlorochromate (PCC) and iodoxybenzoic acid (IBX) reagents. Using a range of hydroxylactams, optimal conversions of these substrates to the corresponding imides was achieved with 50 equivalents of freshly prepared NiO2 in refluxing toluene over 5–32 h reaction times. By comparison, oxidations of the same substrates using PCC/silica gel (three equivalents) and IBX (three equivalents) required oxidation times of 1–3 h for full conversion but required lengthier purification. While nominal amounts (~25 mg) of substrate hydroxylactams were used to ascertain conversion, scale-up procedures using all three methods gave good to excellent isolated yields of imides.

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.

Oxidative Desymmetrization of Isoindolines Realized by tert -Butyl Nitrite (TBN) Initiated Radical sp 3C-H Activation Relay (CHAR)

An oxidative desymmetrization of isoindolines was realized by TBN initiated radical sp 3C-H activation relay (CHAR), providing a series of ω-hydroxylactams in high yields. This reaction exhibits broad substrate scope and functional group tolerance, and even N -alkyl iso-indolines can be well tolerated. The mechanistic study shows that the C-H bond oxidation, dioxygen trapping and intramolecular 1,5-H shift might be the key steps to achieve the oxidative desymmetrization.

Multimetallic iridium-tin (Ir-Sn3) catalyst in N-acyliminium ion chemistry: Synthesis of 3-substituted isoindolinones via intra- and intermolecular amidoalkylation reaction

The multimetallic iridium-tritin (Ir-Sn3) complex [Cp*Ir(SnCl3)2{SnCl2(H2O) 2}] (1) proved to be a highly effective catalyst towards C-OH bond activation of γ-hydroxylactams, leading to a nucleophilic substitution reaction known as the α-amidoalkylation reaction. Catalyst 1 can be easily synthesized from the reaction of (pentamethylcyclocyclopentadienyl)iridium dichloride dimer {[Cp*IrCl2]2} and tin(II) dichloride (SnCl2). In terms of catalyst loading, reaction conditions and yields of the product formed, 1 is found to be superior compared to classical Lewis acid catalysts. Different carbon (arenes, heteroarenes, allyltrimethylsilane, 1,3-dicarbonyls) and heteroatom (alcohols, thiols, amides and sulfonamides) nucleophiles have been successfully employed in the intramolecular and intermolecular alkylations, as well as in heterocyclization reactions. In the majority of cases good to excellent yields of 3-substituted isoindolinones and 5-substituted pyrrolidin-2-ones have been obtained. Besides, the reactions are also atom economical and salt free. It is proposed that the multimetallic Ir-Sn3 catalyst behaves as a mild and selective Lewis acid to activate the γ-hydroxylactam towards the formation of the N-acyliminium ion; the latter being trapped by potent nucleophiles leading to the desired products.

Synthesis and antiplasmodial activity of some 1-azabenzanthrone derivatives

Some synthetic 1-azabenzanthrones (7H-dibenzo[de,h]quinolin-7-ones) are weakly to moderately cytotoxic, suggesting that they might also show antiparasitic activity. We have now tested a small collection of these compounds in vitro against a chloroquine-re

Intermolecular and intramolecular α-amidoalkylation reactions using bismuth triflate as the catalyst

(Chemical Equation Presented) Bismuth(III) triflate was found to promote the formation of stable cyclic N-acyliminium species in remarkable catalytic amounts (1 mol %). The α-amidoalkylation process seems to be effective in intermolecular and intramolecul