18804-66-5

Upstream product

• 18804-77-8 ethyl 3-oxo-2-(p-tolylhydrazono)butanoate 
• 2028-84-4 p-methylbenzenediazonium chloride 
• 141-97-9 ethyl acetoacetate 
• 140244-83-3 (Z)-(4-methylphenyl)azo tert-butyl sulfide 
• 67-64-1 acetone 

Downstream Products

• 112657-80-4 bis-(p-tolylhydrazono-isopropylidene)-hydrazine 
• 924310-02-1 7-amino-2-p-tolyl-2H-thieno[3,4-d]pyridazin-1-one 
• 128639-58-7 5-methyl-3-oxo-2-p-tolyl-2,3-dihydropyridazine-4-carbonitrile 
• 1414846-56-2 1-[6-(methylsulfonylmethyl)-1,4-di-p-tolyl-1,6-dihydropyridazin-3-yl]ethanone 
• 1414846-52-8 3-acetyl-6-(methylsulfonylmethyl)-5-nitro-1,4-di-p-tolyl-1,4,5,6-tetrahydropyridazine 
• 1414846-47-1 (Z)-1-(5-(2-(methylthio)vinyl)-1,4-di-p-tolyl-1H-pyrazol-3-yl)ethanone 
• 1414846-48-2 (E)-1-(5-(2-(methylthio)vinyl)-1,4-di-p-tolyl-1H-pyrazol-3-yl)ethanone 
• 1414846-39-1 (E)-3-acetyl-4-(4-methylstyryl)-5-(methylthio)-1-p-tolyl-1H-pyrazole 

Relevant academic research and scientific papers

Microwaves in organic synthesis: Synthesis of pyridazinones, phthalazinones and pyridopyridazinones from 2-oxo-arylhydrazones under microwave irradiation

The phenylhydrazones 1a-d condensed with ethyl cyanoacetate to yield pyridazinones 2a-d that reacted with sulphur in presence of piperidine to yield the aminothienopyridazineones 3a,b that reacted with electron poor olefins and acetylenes to yield phthala

An easy access to 2-oxohydrazones via electrophilic α-p-tolylhydrazonylation of ketone enolates with tert-butyl p-tolylazo sulfide

The title reaction conveniently furnishes, as the sole or main products, α-(p-tolylhydrazono)ketones or their N-methylderivatives (H+ or MeI quenching of the final mixture, respectively). Although the method fails with ketones having a secondary alkyl group bonded to the carbonyl, yields are otherwise more than satisfactory and particular interest is attached to the hydrazonylation of the methyl group in methyl ketones.

Behaviour of Arylazo tert-Butyl Sulfides with Ketone Enolates. Competition between SRN1 α-Arylation and Azocoupling Reactions.

(Z)-Arylazo tert-butyl sulfides 1a-i react, in DMSO and at room temperature, with potassium acetone enolate to give good yields of 1-aryl-2-propanones via spontaneous SRN1 dark reactions. α-Phenylation of pincolone and acetophenone enolates by 1a likewise occurs in excellent yields.In agreement with the involvement of an electron-transfer catalyzed chain process, the reaction of the 4-bromo derivative 1n with pinacolone enolate gives mainly the bis-substitution product 13.With azosulfides 1j-m the arylation pathway competes with a base-induced thiol elimination eventually leading, depending on the structure of the azosulfide, to indazoles 8 or 11 and/or to 2-oxopropanal arylhydrazones 9, 10 or 12.