91093-59-3

Upstream product

• 104-03-0 4-nitrobenzeneacetic acid 
• 530-62-1 1,1'-carbonyldiimidazole 

Downstream Products

• 1460-05-5 p-nitrophenylacetaldehyde 
• 1236197-94-6 4-methyl-3-(4-nitrophenyl)-2H-chromen-2-one 
• 2594-09-4 N-hydroxy-2-(4-nitrophenyl)acetamide 
• 120049-02-7 dimethyl (imidazol-1-yl)fumarate 
• 123331-44-2 Dimethyl 7-(4-Nitrophenyl)imidazo<1,2-a>pyridine-5,6-dicarboxylate 

Relevant academic research and scientific papers

An Environmentally Sustainable Mechanochemical Route to Hydroxamic Acid Derivatives

An operationally simple, and cost efficient conversion of carboxylic acids into hydroxamic acid derivatives via a high-energy mechanochemical activation is presented. This ball milling methodology was applied to a wide variety of carboxylic acids dramatically improving purification issues associated with this class of molecules, which still remain one of the main bottlenecks of classical methodologies. (Figure presented.).

Practical Chemoselective Acylation: Organocatalytic Chemodivergent Esterification and Amidation of Amino Alcohols with N-Carbonylimidazoles

Chemoselective transformations are a cornerstone of efficient organic synthesis; however, achieving this goal for even simple transformations, such as acylation reactions, is often a challenge. We report that N-carbonylimidazoles enable catalytic chemodivergent aniline or alcohol acylation in the presence of pyridinium ions or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), respectively. Both acylation reactions display high and broad chemoselectivity for the target group. Unprecedented levels of chemoselectivity were observed in the DBU-catalyzed esterification: A single esterification product was obtained from a molecule containing primary aniline, alcohol, phenol, secondary amide, and N?H indole groups. These acylation reactions are highly practical as they involve only readily available, inexpensive, and relatively safe reagents; can be performed on a multigram scale; and can be used on carboxylic acids directly by in situ formation of the acylimidazole electrophile.

A novel synthesis of 3-aryl coumarins and evaluation of their antioxidant and lipoxygenase inhibitory activity

A series of coumarin analogues bearing a substituted phenyl ring on position 3 were synthesized via a novel methodology, through an intermolecular condensation reaction of 2-hydroxyacetophenones and 2-hydroxybenzaldehyde, with imidazolyl phenylacetic acid active intermediates. The in vitro antioxidant activity of the synthesized compounds was evaluated using two different antioxidant assays (radical scavenging ability of DPPH stable free radical and inhibition of lipid peroxidation induced by the thermal free radical AAPH). Moreover, the ability of the compounds to inhibit soybean lipoxygenase was determined as an indication of potential anti-inflammatory activity.

Regiospecific Synthesis, Structure, and Fluorescence Properties of Highly Substituted Imidazopyridines and Pyridobenzimidazoles

1-(Arylacetyl)imidazoles 1 react with acetylenedicarboxylic esters to provide highly functionalized imidazopyridines 2 in up to 89percent yield.The scope and limitations of this novel condensation reaction have been investigated, and a mechanistic interpretation is presented.A strong effect on the yield of this reaction is observed for electron-donating and electron-withdrawing substituents in the para position of the aryl ring.Moreover, the transformation is shown to proceed in a regiospecific manner starting with 4,5-unsymmetrically substituted 1-(arylacetyl)imidazoles (1d-g) and is extended to the synthesis of the corresponding pyridobenzimazoles 12.The crystal structure of derivative 2a has been determined by X-ray analysis.Imidazopyridines 2 and pyridobenzimidazoles 12, obtained by this procedure, are highly fluorescent in the visible region with characteristically large Stokes shifts.