4999-94-4

Usage

Structure

Dimethyl ester derivative of 1H-1,2,3-triazole-4,5-dicarboxylic acid and 4-nitrophenol

Functional groups

Ester, nitro, triazole, and carboxylic acid groups

Appearance

Unknown, but likely a solid or crystalline material

Solubility

Likely soluble in organic solvents such as ethanol, methanol, or dimethyl sulfoxide (DMSO)

Stability

Stable under normal conditions, but may decompose upon exposure to heat, light, or strong acids/bases

Reactivity

Reacts with nucleophiles, such as amines or thiols, to form various heterocyclic compounds

Applications

Used in organic synthesis as a building block for heterocyclic compounds, and studied for potential pharmacological and biological activities, such as antimicrobial and antiviral properties

Potential uses

Development of new drug candidates and other biologically active molecules

Safety

Unknown, but should be handled with care due to the presence of a nitro group, which can be potentially explosive under certain conditions. Appropriate safety measures should be taken when working with 1H-1,2,3-Triazole-4,5-dicarboxylic acid, 1-(4-nitrophenyl)-, dimethyl ester.

Upstream product

• 762-42-5 dimethyl acetylenedicarboxylate 
• 1516-60-5 4-nitrophenyl azide 
• 1829-60-3 dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate 
• 1829-60-3 dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate 
• 19019-88-6 7-isopropylidene-2,3-dicarbomethoxynorbornadiene 
• 947-57-9 dimethyl bicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate 

Downstream Products

• 156361-37-4 C₁₀H₁₀N₈O₄ 

Relevant academic research and scientific papers

1,2,3-triazole[4,5-d]pyridazines-II. New derivatives tested on adenosine receptors

This paper reports the synthesis and biological evaluation towards A1 and A2 adenosine receptors of new 1,2,3-triazole[4,5-d]pyridazines bearing lipophilic substituents in the 1 position. Some 1-benzyl-4-substituted amino derivatives

SITE-SELECTIVITY OF 1,3-DIPOLAR CYCLOADDITIONS TO 2,3-DIMETHOXYCARBONYL-7-OXABICYCLO-HEPTADIENE

Site-selectivity of dipolar cycloaddition to the title compound was studied.Azomethine X afforded a 1:1 cycloadduct XI at the deactivated double bond at room temperature;upon thermolysis at 110 degC it afforded the acetylated enamine XIII, wich was formed wia a direct cycloaddition at the mentioned temperature.The cycloaddition course was investigated in various solvents;the enamine XIV formed by solvolysis of XIII was the final products in methanol.Cycloaddition of title compound to azides, benzoylnitrile N-oxide and C-acetyl-N-phenylnitrilimine furnished the product of cycloreversion instead of the not isolable 1:1 cycloadducts.5-Azido-2-furancarbaldehyde and 4-nitrophenylazide yielded cycloaddition products to both multiple bonds in an approximately 1:1 ratio: HN3, tosylazide,benzoylnitrile N-oxide and C-acetyl-N-phenylnitrilimine gave the addition products to the deactivated double bond.The solvent-effect of site-selectivity of 1,3-dipolarcycloaddition was inwestigated and the title compound was found to be an exellent synthetic equivalent for acetylene and dimethyl butinedioate.

SITE SELECTIVITY IN THE REACTIONS OF 1,3-DIPOLES WITH NORBORNADIENE DERIVATIVES

The cycloadditions of arylazides, benzonitrile oxides and diphenylnitrile imine to norbornadiene derivatives 1a-c showed varying degree of site- and stereo-selectivity.With dipolarophile 1a arylazides and benzonitrile oxides attack, preferentially, the electron-poor tetrasubstituted double bond, while in the case of 1b and 1c is the substituted double bond which enters the cycloaddition.By contrast, 2-diazopropane and C-phenyl-N-methylnitrone react with the sole tetrasubstituted double bond of 1a-c in stereo- and site-specific cycloadditions.The quantitative evaluation of the two possible reaction paths was performed by glc analysis.The compounds detected were those arising from Diels-Alder cycloreversions of the thermally labile intermediate adducts 2 and 3 (Scheme 1).The results were rationalized on the basis of a qualitative perturbation treatment which considers frontier orbital interactions only.