2009-97-4

Usage

Uses

Used in Chemical Synthesis:
Ethyl diazoacetoacetate is used as a reagent in chemical synthesis for the preparation of various organic compounds. Its reaction with arylalkylamines and diarylamines, catalyzed by Rh2(OAc)4, allows for the formation of complex organic molecules with potential applications in various industries.
Used in Pharmaceutical Industry:
Ethyl diazoacetoacetate is used as an intermediate in the synthesis of pharmaceutical compounds. Its ability to participate in Rh2(OAc)4-catalyzed reactions with amines makes it a valuable component in the development of new drugs and therapeutic agents.
Used in Research and Development:
Ethyl diazoacetoacetate is used as a research compound for studying the reactions of diazo compounds with various amines. This research can lead to the discovery of new reaction pathways and the development of novel organic compounds with potential applications in various fields.

Synthesis Reference(s)

Tetrahedron Letters, 5, p. 2285, 1964 DOI: 10.1002/lipi.19640660210

InChI:InChI=1/C6H8N2O3/c1-3-11-6(10)5(8-7)4(2)9/h3H2,1-2H3

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 75-36-5 acetyl chloride 
• 5408-04-8 ethyl 2-hydroxyimino-3-oxobutanoate 
• 141-97-9 ethyl acetoacetate 
• 624-90-8 Methanesulfonyl azide 
• 1723-25-7 ethyl 2,3-dioxobutyrate 
• 2158-14-7 4-acetamidobenzenesulfonyl azide 
• 30805-07-3 2-azido-4,6-dimethoxy-1,3,5-triazine 
• 870-46-2 t-butoxycarbonylhydrazine 
• 941-55-9 4-toluenesulfonyl azide 
• 506-96-7 Acetyl bromide 
• 20363-85-3 diethyl mercuribis(diazoacetate) 

Downstream Products

• 27049-64-5 5-methyl-1-phenyl-1H-1,2,3-triazole-4-carboxylic acid ethyl ester 
• 19374-75-5 3-methyl-1-phenylpyrazole-4,5-dione 4-phenylhydrazone 
• 13339-97-4 3-oxo-2-(triphenylphosphoranylidene-hydrazono)-butyric acid ethyl ester 
• 41892-81-3 ethyl 2-acetyl-4-oxopentanoate 
• 145627-51-6 ethyl 5-methyl-2-methylimino-1,3-oxathiole-4-carboxylate 
• 78978-83-3 ethyl-2-(benzoylimino)-5-methyl-1,3-oxathiol-4-carboxylate 
• 62596-45-6 3-(2-methyl-5-(4-methoxyphenyl))furoic acid ethyl ester 
• 2436-79-5 diethyl 2,4-dimethylpyrrole-3,5-dicarboxylate 
• 609-08-5 Diethyl methylmalonate 
• 220861-66-5 5-(4-benzoylamino-phenyl)-2-diazo-5-hydroxy-3-oxo-pentanoic acid ethyl ester 
• 501677-14-1 ethyl 2-diazo-3-oxo-5-(N-tosyl)amino-5-phenylpentanoate 
• 501677-15-2 ethyl 2-diazo-3-oxo-5-(N-tosyl)amino-5-(2-methylphenyl)pentanoate 

Relevant academic research and scientific papers

A new method for the synthesis of N-protected β-amino-α-keto esters from fluoroalkanesulfonylazides and α-keto esters

In the presence of a secondary amine, treatment of α-keto esters with fluoroalkanesulfonyl azides at room temperature afforded N-sulfonyl protected β-amino-α-keto esters in good to excellent yields. This reaction provided a novel, direct and convenient access to N-sulfonyl protected β-amino-α-keto esters from α-keto esters and fluoroalkanesulfonyl azides under mild conditions. However, the reaction of fluoroalkanesulfonyl azides with β-ketoester enamines afforded two products: N-fluoroalkanesulfonyl amidines and diazoacetate. The reaction mechanism is discussed.

Solvent-Directed Click Reaction between Active Methylene Compounds and Azido-1,3,5-triazines

A novel solvent-directed click reaction between active methylene compounds and azido-1,3,5-triazines has been developed. In aqueous solution, the regiospecific trisubstituted 1,2,3-triazole products are quickly synthesized in high yields under mild conditions and easy to separate without column chromatography. This click reaction is controlled by the protonation of a nitrogen anion intermediate, and the postulated mechanism is substantiated by DFT calculations.

Development of a povarov reaction/carbene generation sequence for alkenyldiazocarbonyl compounds

Rings aplenty: A HOTf-catalyzed (Tf=trifluoromethanesulfonyl) Povarov reaction of alkenyldiazo species has been developed and delivers diazo-containing cycloadducts stereoselectively (see scheme). The resulting cycloadducts provide access to six- and seven-membered azacycles through the generation of metal carbenes as well as the functionalization of diazo group. Copyright

Efficient solid/liquid phase-transfer catalytic diazo transfer synthesis

A simple and efficient solid/liquid phase-transfer catalytic diazo transfer reaction for the synthesis of diazocarbonyl, diazophosphonyl, and diazophosphinyl compounds is reported. Copyright

Rh(III)-catalyzed chelation-assisted intermolecular carbenoid functionalization of α-imino Csp3-H bonds

A Rh(iii)-catalyzed cross-coupling/cyclization cascade of α-imino Csp3-H bonds with donor/acceptor α-acyl diazocarbonyl compounds has been developed. This novel transformation involves ligand-directed Csp3-H bond functionalization with carbenoids under the pyridine-chelation assistance, and offered an efficient access to synthetically versatile polysubstituted N-(2-pyridyl)pyrroles with a broad range of functional group tolerance.

A dual-protein cascade reaction for the regioselective synthesis of quinoxalines

In this work, an efficient dual-protein (lipase and hemoglobin) system was successfully constructed for the regioselective synthesis of quinoxalines in water. A set of quinoxalines were obtained in high yields under optimal reaction conditions. This dual-protein method exhibited a regioselectivity higher than those of previously reported methods. This study not only provides a green and mild strategy for the synthesis of quinoxalines but also expands the application of lipase and hemoglobin in organic synthesis.

Azidotris(diethylamino)phosphonium bromide: A self-catalyzing diazo transfer reagent

Acidic methylene compounds are conveniently converted to diazo compounds in high yields by azidotris(diethylamino)phosphonium bromide, 1, in diethyl ether using only a catalytic amount of base. The product diazo compounds are easily separated from the co-product hexaethylphosphorimidic triamide hydrobromide.

Transition metal-free steric controlled one-pot synthesis of highly substituted N-amino 1,2,3-triazole derivatives via diazo transfer reaction from β-keto esters

An efficient, simple protocol for the one-pot synthesis of N-amino 1,2,3-triazole from β-keto esters has been described. This method involves diazo transfer reaction into in situ generated hydrazones using imidazole sulfonyl azide as the nitrogen source.

Rh-Catalyzed Coupling of Acrylic/Benzoic Acids with α-Diazocarbonyl Compounds: An Alternative Route for α-Pyrones and Isocoumarins

A coupling of acrylic acids/benzoic acids with α-diazocarbonyl compounds has been realized by a combined catalytic system of rhodium catalyst and Zn(OAc)2 additive. The presence of Zn(OAc)2 obviously accelerates the C(sp2)

Exporting Metal-Carbene Chemistry to Live Mammalian Cells: Copper-Catalyzed Intracellular Synthesis of Quinoxalines Enabled by N?H Carbene Insertions

Implementing catalytic organometallic transformations in living settings can offer unprecedented opportunities in chemical biology and medicine. Unfortunately, the number of biocompatible reactions so far discovered is very limited, and essentially restricted to uncaging processes. Here, we demonstrate the viability of performing metal carbene transfer reactions in live mammalian cells. In particular, we show that copper (II) catalysts can promote the intracellular annulation of alpha-keto diazocarbenes with ortho-amino arylamines, in a process that is initiated by an N-H carbene insertion. The potential of this transformation is underscored by the in cellulo synthesis of a product that alters mitochondrial functions, and by demonstrating cell selective biological responses using targeted copper catalysts. Considering the wide reactivity spectrum of metal carbenes, this work opens the door to significantly expanding the repertoire of life-compatible abiotic reactions.