130625-23-9

Upstream product

• 39149-75-2 ethyl 2-benzyl-2-bromo-3-oxobutanoate 
• 620-79-1 Ethyl 2-benzylacetoacetate 
• 141-97-9 ethyl acetoacetate 
• 100-39-0 benzyl bromide 

Downstream Products

• 51439-57-7 ethyl 2-acetamidocinnamate 
• 130625-25-1 ethyl 2-benzylimino-3-oxobutanoate 
• 130625-26-2 2-[(E)-Acetylimino]-3-phenyl-propionic acid ethyl ester 
• 100-52-7 benzaldehyde 
• 62436-67-3 ethyl (Z)-2-acetylamino-3-phenyl-2-propenoate 
• 66299-29-4 (E)-N-Acetyl-α,β-didehydrophenylalanin-ethylester 
• 59223-88-0 ethyl 2-acetamido-2-methoxy3-phenylpropanoate 

Relevant academic research and scientific papers

Iron-Catalyzed Acyl Migration of Tertiary α-Azidyl Ketones: Synthetic Approach toward Enamides and Isoquinolones

This paper reports that tertiary α-azidyl phenyl ketones can be transformed into enamides by treatment with FeBr2 at elevated temperature in DMF. The reaction proceeds via 1,2-benzoyl migration from α-carbon to the nitrogen atom, accompanied by expulsion of a nitrogen molecule. This protocol is suitable for the synthesis of N-(cyclopent-1-en-1-yl)benzamides, N-(cyclohex-1-en-1-yl)benzamides, and N-benzoyl-α-methyl enamines and provides a convenient approach toward isoquinolones.

Photochemistry of 2-azido-2-alkyl-3-oxobutanoic esters and amides

Photolysis of 2-alkyl-2-azido-3-oxobutanoic esters and amides gave products resulting from alkyl or acyl migration onto nitrogen.The resulting ketimines could be isolated in moderate purity, but the N-acyl imines were rapidly converted into solvation products or enamides (N-acylated dehydroamino acid esters) resulting from double bond migration.Mechanisms for formation of these products are discussed.The N-(2-azido-2-methyl-3-oxobutanoyl) derivative of the diketopiperazine from L-valyl-L-proline gave a stereoisomer of the cyclol tripeptide unit of ergovaline.