33876-67-4

Upstream product

• 146767-34-2 4-Methylphenylazo tert-butyl sulfide 
• 98-86-2 acetophenone 
• 2028-84-4 p-methylbenzenediazonium chloride 
• 614-20-0 3-oxo-3-phenylpropionic acid 
• 34438-71-6 acetophenone enolate 

Downstream Products

• 1265801-93-1 3-hydroxy-1-phenyl-2-(2-p-tolylhydrazono)propan-1-one 
• 1265802-08-1 3-amino-6-benzoyl-5-phenyl-2-p-tolyl-2,5-dihydropyridazine-4-carbonitrile 
• 1265802-14-9 3-amino-6-benzoyl-5-phenyl-2-p-tolyl-2,5-dihydropyridazine-4-carboxylic acid ethyl ester 
• 1414846-55-1 [6-(methylsulfonylmethyl)-1,4-di-p-tolyl-1,6-dihydropyridazin-3-yl](phenyl)methanone 
• 1414846-51-7 3-benzoyl-6-(methylsulfonylmethyl)-5-nitro-1,4-di-p-tolyl-1,4,5,6-tetrahydropyridazine 
• 1414846-45-9 (Z)-(5-(2-(methylthio)vinyl)-1,4-di-p-tolyl-1H-pyrazol-3-yl)(phenyl)methanone 
• 1414846-46-0 (E)-(5-(2-(methylthio)vinyl)-1,4-di-p-tolyl-1H-pyrazol-3-yl)(phenyl)methanone 
• 1414846-38-0 (E)-3-benzoyl-(4-methylstyryl)-5-(methylthio)-1-p-tolyl-1H-pyrazole 

Relevant academic research and scientific papers

Improved synthesis of 2-arylhydrazono-3-hydroxy-1-propanones and their utility in efficient synthesis of pyridazine derivatives

Reaction of 2-arylhydrazono-1-phenylethanones 2a-c with formaldehyde either in presence of montmorillonite K10 or by simply stirring in methanol and TEA leads to selective synthesis of 2-arylhydrazono-3-hydroxy-1-phenylpropan-1-one derivatives 3a-c in high yield. Heating 1a with N-phenylmaleimide in DPE/DABCO using microwave irradiation for 5 minutes at 200 °C results in a 73% yield of pyrrolo[3, 4-c]pyridazine 8. Compounds 2a-c react with benzylidenemalononitriles 9a or ethyl 2-cyanocinnamate 9b in refluxing ethanol and piperidine or β-chitosan to yield new pyridazine derivatives 10a-f which are converted into pyridazinones 11a-c upon reflux in acetic/hydrochloric acids mixture. ARKAT-USA, Inc.

A novel approach to 1-aryl-2-(p-tolylazo)alkenes from alkyl aryl ketones

1-Aryl-2-(p-tolylazo)alkenes were synthesized starting from alkyl aryl ketones in good overall yield. The employed three-step procedure involves: i) α-p-tolylhydrazonylation of ketone enolates with tert-butyl p- tolylazosulfide 1; ii) selective reduction of the carbonyl function of the obtained α-p-tolylhydrazono ketones 3 with NaBH4; iii) dehydration of the ensuing hydrazono alcohols 4 either in an Et2O/dil. H2SO4 two-phase system or in pyridine/acetie anhydride.

α-arylation vs. α-arylhydrazonylation of alkyl aryl ketones with arylazo tert-butyl sulfides

Potassium enolates of alkyl aryl ketones react selectively in DMSO with phenylazo 1a and 4-methylphenylazo tert-butyl sulfide 1b undergoing respectively effective α-phenylation via S(RN)1 and α-(4-methylphenyl)hydrazonylation via elimination-addition.

COMPETITIVE PATHWAYS IN THE REACTION BETWEEN AROMATIC AZOSULFIDES AND ENOLATES IN DMSO

The outcome of the reaction between azosulfides 1 and ketone enolates is influenced by the presence of suitable alkyl substituents on the aryl moiety of 1.The system can thus be conveniently exploited for the selective synthesis of different classes of derivatives of remarkable applicative interest, namely α-aryl ketones, α-arylhydrazono ketones, or indazoles.