55315-86-1

Upstream product

• 2107-69-9 5,6-dimethoxy-1-indanone 
• 62-53-3 aniline 
• 22792-07-0 (3,4-dimethoxyphenyl)(pyrrolidin-1-yl)methanone 
• 103-71-9 phenyl isocyanate 
• 5653-40-7 2-Amino-4,5-dimethoxybenzoic acid 
• 201230-82-2 carbon monoxide 
• 110190-08-4 1,2-diiodo-4,5-dimethoxybenzene 

Relevant academic research and scientific papers

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.

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.

Ruthenium(II)-Catalyzed C-H Activation with Isocyanates: A Versatile Route to Phthalimides

A cationic ruthenium(II)-complex was utilized in the efficient synthesis of phthalimide derivatives by C- H activation with synthetically useful amides. The reaction proceeded through a mechanistically unique insertion of a cycloruthenated species into a C- Het multiple bond of isocyanate. The novel method also proved applicable for the synthesis of heteroaromatic unsymmetric diamides as well as a potent COX-2 enzyme inhibitor. A convenient route to phthalimide: A convergent method for the ruthenium(II)-catalyzed imidation of easily accessible benzamides by C- H functionalization was developed (see scheme). The methodology was successfully applied to the preparation of synthetically challenging unsymmetrical heteroaromatic diamides and proved amenable to a step-economic synthesis of a potent COX-2 enzyme inhibitor.

Preparation of N-Substituted Phthalimides by Palladium-Catalyzed Carbonylation and Coupling of o-Dihalo Aromatics and Primary Amines

A novel method for the formation of N-substituted phthalimides is described which is based on the palladium-catalyzed carbonylation and coupling of o-dihalo aromatics and primary amines.Optimal conditions established for the reaction using o-diiodobenzene and aniline were DMAc (0.2 M), 115 deg C, 90 psi of CO, 3 percent PdCl2L2, and 2.4 equiv of DBU.This process is tolerant of a wide variety of functional groups and gives good yields of the desired products.Variables such as temperature, catalyst type and loading, CO pressure, solvent, and base were examined to optimize this reaction.The reaction of aniline with 1,2-dibromocyclopentene under similar conditions gave a variety of products.