6296-09-9

Usage

Uses

Used in Pharmaceutical Industry:
(3Z)-3-[(4-methylphenyl)imino]-2-benzofuran-1(3H)-one is used as a pharmaceutical intermediate for the development of new drugs. Its distinct chemical structure allows it to be a versatile building block in the synthesis of various medicinal compounds, potentially leading to the discovery of novel therapeutic agents.
Used in Organic Synthesis:
In the field of organic synthesis, (3Z)-3-[(4-methylphenyl)imino]-2-benzofuran-1(3H)-one serves as a key intermediate for the preparation of complex organic molecules. Its unique structure and functional groups enable it to be a valuable component in the synthesis of a wide range of organic compounds, including those with potential applications in materials science, agrochemicals, and other specialty chemicals.

Upstream product

• 106-49-0 p-toluidine 
• 88-95-9 Phthaloyl dichloride 
• 601-70-7 3,3-dichlorophthalide 
• 19336-70-0 N-p-tolyl-phthalamic acid 
• 88-99-3 benzene-1,2-dicarboxylic acid 

Relevant academic research and scientific papers

Synthetic strategy and antiviral evaluation of diamide containing heterocycles targeting dengue and yellow fever virus

High-Throughput screening of a subset of the CD3 chemical library (Centre for Drug Design and Discovery; KU Leuven) provided us with a lead compound 1, displaying low micromolar potency against dengue virus and yellow fever virus. Within a project aimed at discovering new inhibitors of flaviviruses, substitution of its central imidazole ring led to synthesis of variably substituted pyrazine dicarboxylamides and phthalic diamides, which were evaluated in cell-based assays for cytotoxicity and antiviral activity against the dengue virus (DENV) and yellow fever virus (YFV). Fourteen compounds inhibited DENV replication (EC50 ranging between 0.5 and 3.4 1/4M), with compounds 6b and 6d being the most potent inhibitors (EC50 0.5 1/4M) with selectivity indices (SI) > 235. Compound 7a likewise exhibited anti-DENV activity with an EC50 of 0.5 1/4M and an SI of >235. In addition, good antiviral activity of seven compounds in the series was also noted against the YFV with EC50 values ranging between 0.4 and 3.3 1/4M, with compound 6n being the most potent for this series with an EC50 0.4 1/4M and a selectivity index of >34. Finally, reversal of one of the central amide bonds as in series 13 proved deleterious to the inhibitory activity.

The reaction of phthalidylidene dichloride with primary amines. Synthesis and X-ray molecular structure of N-substituted phthalisoimides

An efficient method for the synthesis of N-substituted phthalisoimides, by reaction of phthalidylidene dichloride with primary amines, is described. The reactions with arylamines, arylenediamincs and alkylenediamines lead to the corresponding phthalisoimides or bisphthalisoimides in nearly quantitative yields. However, the reactions with alkylamines are not useful because of the relatively high nucleophilicity of alkylamines. Certain particular behaviours of arylamines, associated with the presence of specific ortho-substituents have been found. The reactions of arylamines bearing an o-hydroxymethyl group provide a convenient method for preparing 2-benzoxazinylbenzoic acids. The X-ray crystallographic structures of N-(2-methoxyphenyl)phthalisoimide 3a and 2-(4H-3.1-benzoxazin-2-yl)benzoic acid 15a have been determined.

A NEW METHOD FOR THE SYNTHESIS OF N-ARYLPHTHALISOIMIDES

N-arylphthalisoimides have been synthesized in almost quantitative yields by the reaction, under very mild conditions, of 3,3-dichlorphthalide with aromatic amines.