184579-16-6

Upstream product

• 153864-61-0 2-Phenylazo-2-(2,2,2-trifluoro-acetoxy)-propionic acid ethyl ester 
• 13732-34-8 ethyl α-(Z-phenylhydrazono)propionate 
• 13732-33-7 ethyl α-(E-phenylhydrazono)propionate 
• 184579-11-1 2-Acetoxy-2-phenylazo-propionic acid ethyl ester 
• 100-39-0 benzyl bromide 
• 65296-08-4 ethyl α-(N,N-dimethylhydrazono)-propionate 
• 100-63-0 phenylhydrazine 

Downstream Products

• 617-35-6 2-oxo-propionic acid ethyl ester 

Relevant academic research and scientific papers

Enantioselective Alkylation of N-Arylhydrazones Derived from α-Keto Esters and Isatin Derivatives through Asymmetric Phase-Transfer Catalysis

The phase-transfer-catalyzed asymmetric alkylation reactions of N-arylhydrazones derived from α-keto-esters and isatin derivatives afford enantioenriched azo compounds that bear a tetra-substituted carbon stereocenter in good yields with high chemo- and enantioselectivity. The alkylation products can be readily converted into chiral amino esters, hydrazine derivatives, and aza-β-lactams without loss of enantiopurity.

Oxidation of hydrazones by hypervalent organoiodine reagents: Regeneration of the carbonyl group and facile syntheses of α-acetoxy and α-alkoxy azo compounds

Various hydrazone derivatives of α-keto esters were prepared. The carbonyl group was readily regenerated in high yield from phenylhydrazones through oxidative hydrolysis using hypervalent organoiodine(III) reagents either bis(trifluoroacetoxy)-iodobenzene (BTIB) in aqueous acetonitrile or hydroxy(tosyloxy)iodobenzene (HTIB) in chloroform. α-Acotxy phenyl- or methylazo compounds were readily synthesized by oxidation of the corresponding hydrazones with iodobenzene diacetate (IBDA) in dichloromethane or acetic acid. α-Methoxy phenyl- or methylazo compounds were also prepared by oxidation of the hydrazones in methanol. The mechanisms of the oxidation reactions are discussed.

Oxidation of phenylhydrazones of α-keto esters with hypervalent organoiodine reagents

α-Ketoacids and ketones can easily be regenerated in high yield from their phenylhydrazones via hydroxy azo compounds upon oxidation with hupervalent iodine reagents.