33886-51-0

Upstream product

• 108-24-7 acetic anhydride 
• 95124-32-6 N-((5-methylfuran-2-yl)methyl)aniline 
• 62-53-3 aniline 
• 150867-03-1 2-formyl-5-methylbenzoic acid 
• 85090-26-2 5-methyl-2-phenylisoindoline-1,3-dione 
• 610-72-0 2,5-dimethylbenzoic acid 
• 22328-43-4 2,5-dimethylbenzoyl chloride 
• 19438-61-0 4-methylphthalic anhydride 

Relevant academic research and scientific papers

Opening of the epoxide bridge in 3a,6-epoxyisoindol-1-ones by the action of bf3et2o in acetic anhydride

The opening of the epoxide bridge in N-substituted 2,3,7,7a-tetrahydro-3a, 6-epoxyisoindol-1-ones by the action of BF3Et2O in acetic anhydride at 25°C over 1 h proceeds through an SN1 mechanism. The allylic type cation formed in the first step is stabiliz

Metal-Free Cascade Formation of Intermolecular C-N Bonds Accessing Substituted Isoindolinones under Cathodic Reduction

An electrochemical protocol for the construction of substituted isoindolinones via reduction/amidation of 2-carboxybenzaldehydes and amines has been realized. Under metal-free and external-reductant-free electrolytic conditions, the reaction achieves the cascade formation of intermolecular C-N bonds and provides a series of isoindolinones in moderate to good yields. The deuterium-labeling experiment proves that the hydrogen in the methylene of the product is mainly provided by H2O in the system.

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.

Isoindolinone Synthesis: Selective Dioxane-Mediated Aerobic Oxidation of Isoindolines

N-Alkyl and N-aryl-isoindolinones were prepared by a dioxane-mediated oxidation of isoindoline precursors. The transformation exhibits unique chemoselectivity for isoindonlines. A chiral tertiary (3°)-benzylic position was not racemized during oxidation, and methyl indoprofen was prepared by late stage oxidation. Mechanistic studies suggest a selective H atom transfer, which avoids many known oxidation (by-)products of isoindolinones.

Copper-Catalyzed sp3 C-H Aminative Cyclization of 2-Alkyl-N-arylbenzamides: An Approach for the Synthesis of N-Aryl-isoindolinones

The synthesis of isoindolinones via copper-catalyzed sp3 C-H functionalization of 2-alkyl-N-substituted benzamides is described. This process does not require the preparation of halogenated substitutes, expensive transition metals, or toxic Sn or CO gas. This method provides an efficient approach to generate various functionalized isoindolinones.

Transition metal free intramolecular selective oxidative C(sp3)-N coupling: Synthesis of N-aryl-isoindolinones from 2-alkylbenzamides

A synthetic method has been developed for the preparation of biologically important isoindolinones including indoprofen and DWP205190 drugs from 2-alkylbenzamide substrates by transition metal-free intramolecular selective oxidative coupling of C(sp3)-H and N-H bonds utilizing iodine, potassium carbonate and di-tert-butyl peroxide in acetonitrile at 110-140 °C.