105020-45-9

Usage

Structure

Methyl ester derivative of 1H-Pyrazole-3-carboxylic acid with a cyano group at the 4-position

Heterocyclic organic compound

Consists of a ring structure containing both carbon and nitrogen atoms

Commonly used in pharmaceutical and agrochemical industries

Used as a building block for the synthesis of various drug candidates and active pharmaceutical ingredients

Potential biological and pharmacological activities

Anti-inflammatory, analgesic, and anti-tumor properties

Potential health and safety hazards

Should be handled with care to avoid adverse effects on health and safety.

Upstream product

• 186581-53-3 diazomethane 
• 35234-87-8 dimethyl 2,3-dicyanofumarate 
• 24153-51-3 diazomethane 
• 105020-46-0 4-Cyan-1,3-pyrazoldicarbonsaeure-dimethylester 
• 105020-40-4 trans-4,5-Dicyan-4,5-dihydro-1H-pyrazol-4,5-dicarbonsaeure-dimethylester 
• 204767-46-4 3-Acetylamino-4-cyano-4,5-dihydro-3H-pyrazole-3-carboxylic acid methyl ester 
• 204767-36-2 (E)-2-Acetylamino-3-cyano-acrylic acid methyl ester 
• 110-89-4 piperidine 
• 108306-82-7 4-Cyano-4H-pyrazole-3,4-dicarboxylic acid dimethyl ester 

Downstream Products

• 105020-37-9 4-Cyan-1-methyl-3-pyrazolcarbonsaeure-methylester 
• 70910-18-8 4-Cyan-1-methyl-5-pyrazolcarbonsaeure-methylester 

Relevant academic research and scientific papers

Synthesis and Transformations of Methyl (E)-2-(Acetylamino)-3-cyanoprop-2-enoate und Methyl (E)-2-(Benzoylamino)-3-cyanoprop-2-enoate, Versatile Reagents for the Preparation of Polyfunctional Heterocyclic Systems

Methyl (E)-2-(acetylamino)-3-cyanoprop-2-enoate (2a) and its 2-benzoyl analog 2b were prepared from the corresponding methyl (Z)-2-(acylamino)-3-(dimethylamino)propenoates 1. Multifunctional compounds 2 are versatile synthons for preparation of polysubstituted heterocyclic systems such as pyrroles 4, pyrimidines 5 and 6, pyridazines 7, pyrazoles 8, 9, and 11, and isoxazoles 10.

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.