57362-82-0

Usage

Uses

Used in Pharmaceutical Industry:
1H-1,2,3-Triazole-4-carboxylic acid, 1-methyl-, methyl ester (9CI) is used as a building block for the synthesis of various medicinal compounds, including potential anticancer agents. Its biological activities, such as antifungal, antibacterial, and antiviral properties, contribute to the development of new drugs with therapeutic benefits.
Used in Agrochemical Industry:
In the agrochemical industry, 1H-1,2,3-Triazole-4-carboxylic acid, 1-methyl-, methyl ester (9CI) serves as a key component in the production of various agrochemicals and insecticides. Its incorporation enhances the effectiveness of these products, providing protection against pests and diseases in agriculture.
Overall, 1H-1,2,3-Triazole-4-carboxylic acid, 1-methyl-, methyl ester (9CI) plays a significant role in both the pharmaceutical and agrochemical industries due to its wide range of applications and biological activities, making it a valuable chemical compound for research and development.

InChI:InChI=1/C5H7N3O2/c1-8-3-4(6-7-8)5(9)10-2/h3H,1-2H3

Upstream product

• 186581-53-3 diazomethane 
• 17640-15-2 methyl cyanoformate 
• 35234-87-8 dimethyl 2,3-dicyanofumarate 
• 24153-51-3 diazomethane 
• 105020-40-4 trans-4,5-Dicyan-4,5-dihydro-1H-pyrazol-4,5-dicarbonsaeure-dimethylester 
• 52745-92-3 methyl (E)-3-nitroacrylate 
• 624-90-8 methyl azide 
• 922-67-8 propynoic acid methyl ester 
• 4967-77-5 methyl 1,2,3-triazole-4-carboxylate 
• 74-88-4 methyl iodide 
• 73499-98-6 5-cyano-1-methyl-1,5-dihydro-[1,2,3]triazole-4,4-dicarboxylic acid dimethyl ester 

Relevant academic research and scientific papers

Some Aspects of the Azide-Alkyne 1,3-Dipolar Cycloaddition Reaction

Some peculiar features of two most commonly used catalytic systems (Cul and CuSOVsodium ascorbate) controlling the regioselectivity of 1,3-dipolar cycloaddition of azides to terminal alkynes have been studied. Their potentialities, main disadvantages, and limitations have been demonstrated by a number of examples, including reactions of low-molecular-weight azides and alkynes containing heterocyclic substituents. The possibility of using novel reagents in click reactions is discussed.

ZnO nanoparticles-mediated regioselective synthesis of methyl-iV-alkylated 1,2,3-triazole-4-carboxylates

The 1,2,3-triazoles are versatile synthetic intermediates of many biologically active compounds, and their N-1 substituted analogues are potential pharmaceutically important derivatives. In this study, an efficient regioselective N-alkylation reaction of

Selective, Orally Active γ-Aminobutyric AcidA α5 Receptor Inverse Agonists as Cognition Enhancers

Nonselective inverse agonists at the γ-aminobutyric acidA (GABA-A) benzodiazepine binding site have cognition-enhancing effects in animals but are anxiogenic and can precipitate convulsions. Herein, we describe novel GABA-A α5 subtype inverse agonists leading to the identification of 16 as an orally active, functionally selective compound that enhances cognition in animals without anxiogenic or convulsant effects. Compounds of this type may be useful in the symptomatic treatment of memory impairment associated with Alzheimer's disease and related dementias.

REACTIONS DES METHYLAZIDE ET PHENYLAZIDE AVEC QUELQUES ALCYNES ET OLEFINES α-NITREES. SYNTHESE REGIOSPECIFIQUE DES 1,2,3 TRIAZOLES

The reactions of alkynes and α-nitro-olefines with methylazide and phenylazide was studied.In contrast to known reactions with alkynes which are non-regioselective, methylazide and phenylazide react regiospecifically with α-nitro-olefines and give only one type of triazole after elimination of HNO2.These reactions are very useful synthetic approaches to 1,2,3 triazoles.

1,3-Dipolar Cycloadditions, 93. - The Astounding Reaction of Dimethyl 2,3-Dicyanofumarate with Diazomethane

The reaction with excess of diazomethane furnished methyl 4-cyano-1-methylpyrazole-5- and -3-carboxylate (2 and 3) as well as the three N-methyl-1,2,3-triazolecarboxylic esters 4-6.A mechanistic study revealed a poly-step sequence.The initial formation of the pyrazoline 8 proceeded normal.Base catalysis effected an equilibration of trans- and cis-2-pyrazoline, 8(*)12, followed by a fragmentation into methyl 4-cyano-3-pyrazolecarboxylate (26) and methyl cyanoformate (32); a 4H-pyrazole is supposed to be the key intermediate.The final products mentioned above emerged from further reaction of 26 and 32 with diazomethane.

THE ASTOUNDING REACTION OF DIAZOMETHANE WITH DIMETHYL 2,3-DICYANOFUMARATE

The title reaction afforded the pyrazole derivatives 3 and 4 as well as the N-methyl-1,2,3-triazolecarboxylic esters 5 - 7.The poly-step sequence was clarified; the key intermediates are the 1-pyrazoline 18, the 2-pyrazoline 2, the 4H-pyrazole 12, the pyrazole 22, and methyl cyanoformate.

ADDITION D' AZIDES A DES OLEFINES TRISUBSTITUEES PAR DES GROUPEMENTS ELECTROATTRACTEURS

The reaction of benzyl, methyl and phenyl azide, with olefins substituted by three electron-withdrawing groups, has been studied.This reaction gives in certain cases only one triazoline (single orientation of the cycloaddition).In other cases, a mixture o