17448-14-5

Upstream product

• 2142-01-0 N-benzylphthalimide 
• 6940-49-4 3-Bromophthalide 
• 103-49-1 dibenzylamine 
• 6295-21-2 3-chloro-1(3H)-isobenzofuranone 
• 100-46-9 benzylamine 
• 117886-88-1 2-formyl benzoyl chloride 
• 222713-05-5 2-benzyl-3-phenylsulfanyl-2,3-dihydro-isoindol-1-one 
• 136918-14-4 phthalimide 
• 87-41-2 2-benzofuran-1(3H)-one 
• 35180-14-4 N-benzylisoindoline 
• 91-13-4 α,α'-dibromo-o-xylene 
• 100-39-0 benzyl bromide 
• 1074-82-4 potassium phtalimide 

Downstream Products

• 104563-11-3 2-benzyl-3-(2-hydroxyphenyl)isoindolin-1-one 
• 104563-10-2 2-Benzyl-3-(4-hydroxy-phenyl)-2,3-dihydro-isoindol-1-one 
• 97132-10-0 3-(carboxymethylthio)-2,3-dihydro-2-(phenylmethyl)-1H-isoindol-1-one 
• 189271-52-1 3-Amino-2-benzyl-2,3-dihydro-isoindol-1-one 
• 408325-00-8 2-benzyl-3-phenylselanyl-2,3-dihydro-isoindol-1-one 
• 222713-05-5 2-benzyl-3-phenylsulfanyl-2,3-dihydro-isoindol-1-one 
• 1373426-72-2 2-benzyl-3-(3,4-dihydro-2H-pyran-5-yl)isoindolin-1-one 
• 1373426-67-5 (E)-2-benzyl-3-(2-phenylethenyl)isoindolin-1-one 
• 1373426-69-7 2-benzyl-3-(2,2-diphenylethenyl)isoindolin-1-one 
• 1373426-70-0 2-benzyl-3-(1H-inden-2-yl)isoindolin-1-one 
• 1373426-71-1 2-benzyl-3-cyclohex-1-en-1-ylisoindolin-1-one 
• 1373426-68-6 2-benzyl-3-(2-phenyl-2-propenyl)isoindolin-1-one 
• 905774-95-0 2-benzyl-3-(1H-indol-3-yl)isoindolin-1-one 

Relevant academic research and scientific papers

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.

Electroselective and Controlled Reduction of Cyclic Imides to Hydroxylactams and Lactams

An efficient and practical electrochemical method for selective reduction of cyclic imides has been developed using a simple undivided cell with carbon electrodes at room temperature. The reaction provides a useful strategy for the rapid synthesis of hydroxylactams and lactams in a controllable manner, which is tuned by electric current and reaction time, and exhibits broad substrate scope and high functional group tolerance even to reduction-sensitive moieties. Initial mechanistic studies suggest that the approach heavily relies on the utilization of amines (e.g., i-Pr2NH), which are able to generate α-aminoalkyl radicals. This protocol provides an efficient route for the cleavage of C-O bonds under mild conditions with high chemoselectivity.

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.

Preparation method of hydroxyl lactam

The invention discloses a preparation method of hydroxyl lactam. The hydroxyl lactam is prepared from cyclic imide shown in a formula (II) through a homogeneous catalytic hydrogenation reaction, wherein R1, R2 and R3 are respectively and independently H,

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.

PdII/AgI-Catalyzed Room-Temperature Reaction of γ-Hydroxy Lactams: Mechanism, Scope, and Antistaphylococcal Activity

The present work reports a PdII/AgI-promoted amidoalkylation reaction involving various γ-hydroxy lactams and C/O/S nucleophiles at room temperature. The dual mode of activation of both the electrophile and nucleophile by in situ generated catalytically active cationic PdII species facilitates the reaction at room temperature. Among the synthesized isoindoline derivatives, three compounds are found to be active against vancomycin and methicillin-resistant S. aureus strain with appreciable MIC values.

Potassium Hydroxide-Catalyzed Chemoselective Reduction of Cyclic Imides with Hydrosilanes: Synthesis of ω-Hydroxylactams and Lactams

Potassium hydroxide-catalyzed hydrosilylation exhibits excellent activity and chemoselectivity for the reduction of cyclic imides under mild reaction conditions. The chemoselectivity of the reduction system may be readily tuned by changing the identity an

Zinc-catalyzed selective reduction of cyclic imides with hydrosilanes: Synthesis of ω-hydroxylactams

Cyclic imides were selectively reduced to the corresponding ω-hydroxylactams in high yields with (EtO)3SiH (triethoxysilane) or PMHS (polymethylhydrosiloxane) under catalysis of zinc diacetate dehydrate [Zn(OAc)2 2H2O] (10%) and tetramethylethylenediamine (TMEDA) (10%). This catalytic protocol showed good functional group tolerance as well as excellent regioselectivity for unsymmetrical imides bearing coordinating groups adjacent to the carbonyl.

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.