198135-19-2

Upstream product

• 60083-22-9 ethyl (2E)-3-oxo-2-(2-phenylhydrazinylidene)butanoate 
• 146000-76-2 C₆H₉N₃O₃ 
• 100-63-0 phenylhydrazine 
• 105-45-3 acetoacetic acid methyl ester 
• 64-17-5 ethanol 
• 198135-47-6 4-(methoxycarbonyl)-5-methyl-1-phenyl-1H-pyrazole-3-carboxylic acid 

Downstream Products

• 268544-98-5 methyl 3-cyclopropylcarboxamido-5-methyl-1-phenyl-4-pyrazolecarboxylate 
• 268544-93-0 methyl 3-tert-butylcarboxamido-5-methyl-1-phenyl-4-pyrazolecarboxylate 
• 1026593-28-1 3-chlorocarbonyl-5-methyl-1-phenyl-1H-pyrazole-4-carboxylic acid methyl ester 
• 198135-47-6 4-(methoxycarbonyl)-5-methyl-1-phenyl-1H-pyrazole-3-carboxylic acid 
• 77936-92-6 5-methyl-1-phenyl-1H-pyrazole-3,4-dicarboxylic acid 

Relevant academic research and scientific papers

Expeditious solid-phase synthesis of pyrazoledicarboxylic acid derivatives by functionalization of resin-bound cyanoformate

Esterification of the Wang resin 5 with the monoamide of oxalic acid (oxamic acid, 7) followed by dehydration of the amide function furnishes the resin-bound cyanoformate 9, which can be elaborated by zinc-catalyzed reaction with β-keto esters. The obtained enamino keto diesters 10a-d react with hydrazines affording, after removal from the solid support, fully substituted pyrazoledicarboxylic acids 12a-n. Optimization of the above sequence and the solid-phase synthesis of a small test-library of 1,5-disubstituted pyrazole-3,4-dicarboxylic acid derivatives are described. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.

Aspects of the chemistry of functionalized 1-phenylpyrazoles available from 1,2-diaza-1,3-butadienes and 2-phenylazo-1,3-dicarbonyl compounds

In the presence of sodium hydride, treatment of 1,2-diaza-1,3-butadienes with 2-phenylazo-1,3-dicarbonyl compounds gave rise to functionalized 1- phenylpyrazole derivatives in good to excellent yields. Pyrazolo[3,4-d]1,6- dihydropyridazin-6(2H)-one derivatives were obtained by the reaction of 5- methyl-4-methoxycarbonyl-3-acetyl-1-phenylpyrazole with different hydrazines.