16035-91-9

Upstream product

• 6335-82-6 phenyl 4-nitrophenylacetate 
• 62-53-3 aniline 
• 50434-36-1 4-nitrophenylacetyl chloride 
• 66003-76-7 Diphenyliodonium triflate 
• 555-21-5 4-Nitrophenylacetonitrile 
• 104-03-0 4-nitrobenzeneacetic acid 
• 3769-82-2 2-(4-nitrophenyl)-1-phenylethanone 
• 4203-31-0 2-diazo-1-(4-nitrophenyl)ethanone 

Downstream Products

• 42003-87-2 N-Phenyl-(4-nitrophenyl)-acetimidsaeure-ethylester 
• 31733-44-5 2-(4-aminophenyl)-N-phenylacetamide 
• 102-07-8 bis(diphenyl)urea 
• 3746-53-0 N-(4-metoxyphenyl)-N'-phenylurea 

Relevant academic research and scientific papers

Copper-catalyzed transformation of alkyl nitriles to N -arylacetamide using diaryliodonium salts

This work reports a simple and efficient method for the copper-catalyzed redox-neutral transformation of alkyl nitriles using eco-friendly diaryliodonium salts and leading to N-arylacetamides. The method features high efficiency, broad substrate scope and good functional group tolerance.

Pharmaceutical composition and method of treating cancer

Cytotoxic compounds containing a phenyl core, amide link(s), an imidazolinone or a propenamide moiety. Also described are pharmaceutical compositions incorporating the cytotoxic compounds and methods for treating cancer. These compounds are cytotoxic against breast, prostate, and leukemia cancer cell lines via dual inhibition of Src kinases and tubulin.

Palladium-catalyzed c-S activation/aryne insertion/coupling sequence: Synthesis of functionalized 2-quinolinones

The insertion of an aryne into a C-S bond can suppress the addition of an S nucleophile to the aryne in the presence of palladium. Catalyzed by Pd(OAc)2, a wide range of α-carbamoyl ketene dithioacetals readily react with arynes to selectively afford functionalized 2-quinolinones in high yields under neutral reaction conditions by a C-S activation/aryne insertion/intramolecular coupling sequence. The attractive feature of the new strategy also lies in the versatile transformations of the alkythio-substituted quinolinone products. Within range: Under palladium catalysis a wide range of α-carbamoyl ketene dithioacetals readily react with arynes to selectively afford 2-quinolinones in high yields under neutral reaction conditions by the title sequence (see scheme). An attractive feature of the new strategy also lies in the versatile transformations of the alkylthio-substituted quinolinones.

Diazotisation Rearrangement of Tosylhydrazones of ortho- and meta-Substituted-benzophenones and α-Substituted-acetophenones (Synthesis of Anilides)

Ortho and meta-substituted-benzophenones (1a-g) and substituted-acetophenones (1h-i) were converted into tosylhydrazones (2a-i) by reacting with p-toluenesulphonyl-hydrazide.Conversion of 2a-i to the anilides (3a-i) was effected with the reagents H2SO4 and NaNO2, and was found to be as facile as in case of the para-substituted-benzophenone hydrozones.

Anticonvulsant activity of some 4-aminophenylacetamides

A series of 4-aminophenylacetamides was prepared and evaluated for anticonsulvant activity. These compounds were prepared during studies designed to determine the relationship between benzamide-like compounds and anticonsulvant effects. Unlike benzamides, these phenylacetamides have a methylene group between the aromatic ring and the amide carbonyl. Consequently, formal conjugation is lost, and the number of conformational degrees of freedom has increased. The compounds were tested in mice against seizures induced by electroshock and pentylenetetrazol, and in the rotorod assay for neurologic deficit. The more active and selective anticonsulvants prepared in this study were those having an additional aromatic ring as part of the substituent on the amide nitrogen. Compound 16, the 4-aminophenylacetamide derived from 2,6-dimethylaniline, was the most potent compound observed (ED50 = 50.50 mg/kg against electroshock-induced convulsions and ED50 = 93.20 mg/kg against pentylenetetrazol-induced convulsions).

Alkaline Hydrolysis of Aryl Phenylacetates and Aryl 4-Nitrophenylacetates. Evidence consistent with an Elimination-Addition Mechanism

Hydrolysis of the substituted phenyl esters of phenylacetic acid is found to be first order each in the ester and hydroxide ion.Hydrolysis is catalysed by general bases and the catalytic coefficients for the substituted phenoxides obey the Broensted relation with β +0.49.The rate of hydrolysis of the esters of 4-nitrophenylacetic acid is independent of in the range employed.Both series of reactions exhibit low solvent isotope effect and high sensitivity to substituents in the leaving group .These datasuggest an E1cB mechanism for the hydrolysis.The keten intermediate envisaged for such a mechanism has been trapped as the anilide when the reactions are conducted in aniline buffers, without any effect on the rate of hydrolysis for variations in .An increase in the DMSO content in the solvent decreases the rate of hydrolysis of the esters of 4-nitrophenylacetic acid, which is explained by an (E1cB)anion mechanism for the hydrolysis.Transfer to aqueous DMSO results in rate accelerations for the esters of phenylacetic acid which can be accounted for by either an (E1cB)Bion pair or (E1cB)reversible mechanism for the hydrolysis.