39149-75-2

Upstream product

• 620-79-1 Ethyl 2-benzylacetoacetate 
• 100-39-0 benzyl bromide 
• 141-97-9 ethyl acetoacetate 

Downstream Products

• 130625-23-9 ethyl 2-azido-2-benzyl-3-oxobutanoate 
• 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 
• 62436-67-3 ethyl (Z)-2-acetylamino-3-phenyl-2-propenoate 
• 66299-29-4 (E)-N-Acetyl-α,β-didehydrophenylalanin-ethylester 

Relevant academic research and scientific papers

Visible-Light-Driven Dearomatization Reaction toward the Formation of Spiro[4.5]deca-1,6,9-trien-8-ones

A visible-light-driven regioselective dearomative cyclization between 2-benzyl-2-bromomalonate and alkynes under mild conditions leading to the formation of spiro[4,5]decanes has been developed. In the presence of H2O, a variety of 2-benzyl-2-b

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.

Chromophore-linked substrate (CLS405): Probing metallo-β-lactamase activity and inhibition

Serine- and metallo-β-lactamases present a threat to the clinical use of nearly all β-lactam antibiotics, including penicillins, cephalosporins, and carbapenems. Efforts to develop metallo-β-lactamase (MBL) inhibitors require suitable screening platforms to allow the rapid determination of β-lactamase activity and efficient inhibition. Unfortunately, the platforms currently available are not ideal for this purpose. Further progress in MBL inhibitor identification requires inexpensive and widely applicable assays. Herein the identification of an inexpensive and stable chromogenic substrate suitable for use in assays of clinically relevant MBLs is described. (6R,7R)-3-((4-Nitrophenoxy)methyl)-8-oxo-7-(2-phenylacetamido) -5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 5,5-dioxide (CLS405) was synthesised in a three-step protocol. CLS405 was then characterised spectroscopically, and its stability and kinetic properties evaluated. With a Δλmax value of 100 nm between the parent and hydrolysis product, a higher analytical accuracy is possible with CLS405 than with commonly used chromogenic substrates. The use of CLS405 in assays was validated by MBL activity measurements and inhibitor screening that resulted in the identification of N-hydroxythiazoles as new inhibitor scaffolds for MBLs. Further evaluation of the identified N-hydroxythiazoles against a panel of clinically relevant MBLs showed that they possess inhibitory activities in the mid- to low-micromolar range. The findings of this study provide both a useful tool compound for further inhibitor identification, and novel scaffolds for the design of improved MBL inhibitors with potential as antibiotics against resistant strains of bacteria. Monitoring MBLs! Resistance to β-lactam antibiotics, mediated by metallo-β-lactamases (MBLs), is an increasing clinical problem. While compounds that target MBLs could be useful antibacterial agents, their identification is hampered by the lack of suitable assay platforms. To this end, CLS405, a chromophore-linked MBL substrate, was developed and its applicability demonstrated by the identification of N-hydroxythiazoles as potential inhibitors against a panel of clinically relevant MBLs. Copyright

Oxidative bromination of ketones using ammonium bromide and oxone

A highly efficient, environmentally safe and economic method for selective α-monobromination of aralkyl, cyclic, acyclic, 1,3-diketones and β-keto esters and α,α-dibromination of 1,3-diketones and β-keto esters without catalyst is reported using ammonium bromide as a bromine source and oxone as an oxidant. The reaction proceeds at ambient temperature and yields range from moderate to excellent. Bromination of unsymmetrical ketones takes place at the less substituted α-position predominantly. Aromatisation of tetralones is also carried out with this reagent system.

Molybdenum(VI) dichloride

A novel and efficient method for the one-pot transformation of β-hydroxycarbonyl compounds to a-brominated 1,3-dicarbonyl compounds is achieved with MoO2Cl2 in the presence of N-bromosuccinimide. All the reactions were carried out un

Rapid and catalyst-free α-halogenation of ketones using N-halosuccinamides in DMSO

α-Halogenation of various carbonyl compounds such as β-keto-esters, cyclic ketones, and lactams with N-halosuccinamides (NBS, NCS, NIS) in the presence of DMSO proceeded very smoothly to give the corresponding α-monohalogenated products in good to excellent yields with high selectivity under catalyst-free conditions. Copyright Taylor & Francis Group, LLC.

A mild and environmentally acceptable synthetic protocol for chemoselective α-bromination of β-keto esters and 1,3-diketones

A wide variety of unsubstituted β-keto esters can be brominated chemoselectively to the corresponding α-monobromo-β-keto esters by using a combination of vanadium pentoxide, hydrogen peroxide and ammonium bromide in a biphasic system, dichloromethane-wate

A green approach for efficient α-halogenation of β-dicarbonyl compounds and cyclic ketones using N-halosuccinimides in ionic liquids

Room temperature ionic liquids (ILs) are used as a green recyclable reaction media for the α-monohalogenation of 1,3-diketones, β-keto-esters and cyclic ketones with N-halosuccinimides in excellent yields in the absence of a catalyst. The recovered ionic liquid was reused five to six times with consistent activity.

A simple and efficient method for α-bromination of carbonyl compounds using N-bromosuccinimide in the presence of silica-supported sodium hydrogen sulfate as a heterogeneous catalyst

α-Bromination of carbonyl compounds (cyclic and acyclic ketones, amides and β-ketoesters) has been achieved efficiently by treatment with N-bromosuccinimide (NBS) and catalyzed by silica-supported sodium hydrogen sulfate (NaHSO4?SiO2

A mild and efficient procedure for α-bromination of ketones using N-bromosuccinimide catalysed by ammonium acetate

Cyclic ketones reacted with N-bromosuccinimide (NBS) catalysed by NH 4OAc in Et2O at 25°C to give the corresponding α-brominated ketones in good yields, while acyclic ketones were efficiently brominated in CCl4 at 80°C.