56156-40-2

Upstream product

• 2684-02-8 benzenediazonium 
• 2829-26-7 N-(4-chlorobenzylidene)-N'-phenylhydrazine 
• 104-88-1 4-chlorobenzaldehyde 
• 100-63-0 phenylhydrazine 
• 149833-49-8 (E)-1-(4-chlorobenzylidene)-2-phenylhydrazine 
• 62-53-3 aniline 

Downstream Products

• 81817-23-4 3-(4-chlorophenyl)benzo[e][1,2,4]triazine 
• 1386384-43-5 (E)-dimethyl 6-chloro-1-(phenyldiazenyl)isoquinoline-3,4-dicarboxylate 
• 10557-51-4 2,3-Diphenyl-5-(p-chlor-phenyl)-tetrazoliumchlorid 
• 17616-61-4 1,5-diphenyl-3-(p-chloro-phenyl)-verdazyl 
• 96461-82-4 3-(4-chloro-phenyl)-benzo[e][1,2,4]triazin-8-ol 
• 96583-43-6 3-(4-chloro-phenyl)-benzo[e][1,2,4]triazine 1-oxide 

Relevant academic research and scientific papers

Triphenyl verdazyl radicals' reactivity with alkyne carboxylates as a synthetic route to 1-(phenyldiazenyl)isoquinoline-3,4-dicarboxylates

A series of 1-(phenyldiazenyl)isoquinoline-3,4-dicarboxylates are synthesized by a unique reaction of triphenyl verdazyl radical with di-substituted electron deficient alkyne carboxylates. This transformation allows for the quick synthesis of this class of compounds in just three steps starting from a hydrazone. A radical mechanism that is consistent for the substitution patterns observed in the series of compounds made is proposed. The final product is obtained by a subsequent retro-Diels-Alder reaction.

Arylations mediated by lead(IV) in the presence of formazan and imine ligands

The use of formazan and imine ligands in arylations of β-dicarbonyl systems by phenyl boronic acid/lead(IV) carboxylates is examined.

Syntheses of formazans under phase-transfer conditions

Several 1,3,5-triarylformazans were synthesized (42-77%) using a new methodology. Azo-coupling of aryldiazonium salts with arylaldehyde arylhydrazones under mild basic conditions in two-phase liquid-liquid media is efficiently promoted by phase-transfer catalysts (onium salts or dicyclohexano-18-crown-6) at 5-25°C. The condensation of benzaldehyde with phenylhydrazine followed by phase-transfer catalyzed azo-coupling with phenyldiazonium chloride (one-pot procedure) gave 1,3,5-triphenylformazan in a 54% yield without isolation of the intermediate benzaldehyde phenylhydrazone. A double azo-coupling reaction of phenyldiazonium chloride with 9 different CH-active compounds afforded corresponding formazan only in the case of phenylpyruvic acid. Reaction in malonamide gave 3-carbamoyl-1,5-diphenylformazan instead of the expected 1,5-diphenylformazan.