220205-99-2

Upstream product

• 161037-54-3 ethyl pentafluorobenzoylpyruvate 
• 4346-59-2 para-methoxyphenyldiazonium chloride 
• 916987-99-0 ethyl-2-hydroxy-4-oxo-4-pentafluorophenylbut-2-enoate 
• 104-94-9 4-methoxy-aniline 

Downstream Products

• 881410-76-0 2-oxo-2-[5,6,7,8-tetrafluoro-1-(4-methoxyphenyl)-4-oxo-1,4-dihydrocinnolin-3-yl]acetic acid 
• 881410-70-4 2,2-dihydroxy-2-[5,6,7,8-tetrafluoro-1-(4-methoxyphenyl)-4-oxo-1,4-dihydrocinnolin-3-yl]acetic acid 

Relevant academic research and scientific papers

Synthesis of fluorocontaining 3-arylhydrazo-2,3,4-triketoesters and their heterocyclization

3-Arylhydrazones of fluorocontaining 2,3,4-triketoesters were prepared for the first time by coupling of aryldiazonium chlorides with esters of fluoroacyl(aroyl)pyruvic acids and their chelates. Reactions of the arylhydrazones with hydrazine hydrate and o-phenylenediamine result in substituted pyrazoles and quinoxalines respectively. Intramolecular cyclization of fluoroaroyl pyruvate arylhydrazones and derivatives thereof provides new possibilities of synthesis of heterocycles from cinnoline series.

Synthesis of fluorinated 2(3)-arylhydrazones of 1,2,3-tri(1,2,3,4-tetra)carbonyl compounds and their heterocyclization reactions

New fluorinated 2-arylhydrazones of 1,2,3-triketones, 2-arylhydrazone-1,2,3-diketo esters and 3-arylhydrazone-1,2,3,4-triketo esters have been prepared by the coupling of fluorine-containing 1,3-keto esters, 1,3-diketones, acyl(aroyl)pyruvic esters and their chelates with aryldiazonium chlorides. The arylhydrazones react with hydrazine hydrate, phenylhydrazine, thiosemicarbazide and hydroxylamine to form the corresponding pyrazole and isoxazole derivatives. Interaction of 3-arylhydrazone-1,2,3,4-diketo esters with o-phenylenediamine results in quinoxaline products. Intramolecular cyclization of the arylhydrazones with pentafluorophenyl substituents leads to cinnolone derivatives.