85090-26-2

Upstream product

• 19438-61-0 4-methylphthalic anhydride 
• 62-53-3 aniline 
• 941-69-5 N-phenyl-maleimide 
• 133870-31-2 (1E,3E)-2-methyl-4-morpholino-1-(phenylthio)buta-1,3-diene 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 1197040-29-1 phenyl isocyanate 
• 52548-14-8 2-iodoyl-5-methylbenzoic acid 
• 103-71-9 phenyl isocyanate 
• 164918-75-6 (3-methylphenyl)(1-pyrrolidinyl)methanone 
• 59746-40-6 pyrrolidin-1-yl(p-tolyl)methanone 
• 99-04-7 m-Toluic acid 
• 99-94-5 p-Toluic acid 
• 40314-06-5 5-methyl-1H-isoindole-1,3-(2H)-dione 
• 71-43-2 benzene 

Downstream Products

• 6833-18-7 4-methyl-N-phenylbenzamide 
• 23099-05-0 3-methyl-N-phenylbenzamide 
• 33886-51-0 6-methyl-2-phenylisoindolin-1-one 
• 134553-14-3 4-(6-diethylaminobenzofuranyl)-N-phenylphthalimide 
• 134508-26-2 4-bromomethyl-N-phenylphthalimide 
• 84839-34-9 5-methyl-anti-7,8-diazabicyclo<2.2.2>oct-5-ene-2,3,7,8-tetracarboxylic acid bis-N-phenylimide 
• 84839-34-9 5-methyl-syn-7,8-diazabicyclo<2.2.2>oct-5-ene-2,3,7,8-tetracarboxylic acid bis-N-phenylimide 

Relevant academic research and scientific papers

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.

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.

Synthesis of imides via palladium-catalyzed three-component coupling of aryl halides, isocyanides and carboxylic acids

A palladium-catalyzed three-component synthesis of acyclic imides from feedstock aryl halides, carboxylic acids and isocyanides through the intermediacy of isoimides has been developed. The key to the success of this approach was controlled isocyanide slow addition and organic/aqueous biphasic conditions. This transition-metal-catalyzed approach features readily available starting materials, atom- and step-economy, good functional group compatibility and gram-scale synthetic capability. Utilization of this new method is illustrated in the late-stage functionalization of drugs Carprofen, Loxoprofen and Flurbiprofen. This strategy has also been successfully applied in the synthesis of cyclic imides including phthalimide, homophthalimide, and 2H-2-benzazepine-1,3-dione derivatives.

Ru-Catalyzed Selective C-H Bond Hydroxylation of Cyclic Imides

We report on cyclic imides as weak directing groups for selective monohydroxylation reactions using ruthenium catalysis. Whereas acyclic amides are known to promote the hydroxylation of the C(sp2)-H bond enabling five-membered ring ruthenacycle intermediates, the cyclic imides studied herein enabled the hydroxylation of the C(sp2)-H bond via larger six-membered ruthenacycle intermediates. Furthermore, monohydroxylated products were exclusively obtained (even in the presence of overstoichiometric amounts of reagents), which was rationalized by the difficulty to accommodate coplanar intermediates once the first hydroxyl group was introduced into the substrate. The same reactivity was observed in the presence of palladium catalysts.

Unmasking Amides: Ruthenium-Catalyzed Protodecarbonylation of N-Substituted Phthalimide Derivatives

The unprecedented transformation of a wide range of synthetically appealing phthalimides into amides in a single-step operation has been achieved in high yields and short reaction times using a ruthenium catalyst. Mechanistic studies revealed a unique, homogeneous pathway involving five-membered ring opening and CO2 release with water being the source of protons.

Palladium-Catalyzed Synthesis of 1H-Indenes and Phthalimides via Isocyanide Insertion

A new and versatile multicomponent domino strategy has been developed for the synthesis of a series of 1H-indene and phthalimide derivatives from simple and readily available starting materials. This process operating under mild conditions shows a broad substrate scope with moderate to excellent yields.

Synthetic method for N-substituted imide

The invention provides a synthetic method for N-substituted imide. According to the method, aromatic ketone and amine are used as substrates, air or oxygen is used as an oxygen source, and cyclic imide is produced under liquid phase conditions under the action of a catalyst. The method is mild in conditions, high in oxidation efficiency and high in product yield; and since the method uses air or oxygen as the oxygen source, the method is economic and environment-friendly and has good application prospect.

Synthesis of cyclic imides (methylphtalimides, carboxylic acid phtalimides and itaconimides) and evaluation of their antifungal potential

Background: This paper describes the synthesis of three different subfamilies of cyclic imides: methylphtalimides, carboxyl acid phtalimides and itaconimides. Methods: Fifteen compounds (five of each sub-family) were obtained by the reaction of appropriat

Cuprous Oxide Catalyzed Oxidative C-C Bond Cleavage for C-N Bond Formation: Synthesis of Cyclic Imides from Ketones and Amines

Selective oxidative cleavage of a C-C bond offers a straightforward method to functionalize organic skeletons. Reported herein is the oxidative C-C bond cleavage of ketone for C-N bond formation over a cuprous oxide catalyst with molecular oxygen as the oxidant. A wide range of ketones and amines are converted into cyclic imides with moderate to excellent yields. In-depth studies show that both α-C-H and β-C-H bonds adjacent to the carbonyl groups are indispensable for the C-C bond cleavage. DFT calculations indicate the reaction is initiated with the oxidation of the α-C-H bond. Amines lower the activation energy of the C-C bond cleavage, and thus promote the reaction. New insight into the C-C bond cleavage mechanism is presented.