40991-78-4

Upstream product

• 5509-99-9 2-morpholino-1-phenyl-2-thioxoethanone 
• 110-91-8 morpholine 
• 201230-82-2 carbon monoxide 
• 98-86-2 acetophenone 
• 4394-85-8 4-morpholinecarboxaldehyde 
• 611-73-4 Benzoylformic acid 
• 591-50-4 iodobenzene 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 120-72-9 indole 
• 1074-12-0 phenylglyoxal hydrate 
• 109-97-7 pyrrole 
• 108-88-3 toluene 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 14677-24-8 3-Morpholinoacrylophenon 

Downstream Products

• 113397-16-3 (±)-7-hydroxy-7-phenyl-4-oxa-1-azabicyclo[4.2.0]octan-8-one 
• 113397-16-3 (±)-7-hydroxy-7-phenyl-4-oxa-1-azabicyclo[4.2.0]octan-8-one 
• 57872-39-6 2‐hydroxy‐1‐morpholino‐2‐phenylethan‐1‐one 

Relevant academic research and scientific papers

2-Oxo-Driven N2 Elimination Induced Decarbonylative Cyclization Reaction in Benzotriazoles to 6-Aminophenanthridines

An efficient functional group induced strategy for the synthesis of 6-aminophenanthridines (6AP) has been developed as a result of an in situ generated novel system "CO-CH(N1N2)". This reaction presents a new mode of N2 ex

One-Pot Synthesis of α-Ketoamides from α-Keto Acids and Amines Using Ynamides as Coupling Reagents

A one-pot strategy for α-keto amide bond formation have been developed by using ynamides as coupling reagents under extremely mild reaction conditions. Diversely structural α-ketoamides were afforded in up to 98% yield for 36 examples. This reaction features advantages such as practical coupling procedure, wide functional group tolerance, and extremely mild conditions and has potential applications in synthetic and medicinal chemistry.

Desulfurizing agent for thioamides

Thioamides treated with thionyl chloride in an ionic liquid were successfully converted into amides.

Preparation method of alpha-carbonyl amide compound

The invention discloses a preparation method of an alpha-carbonyl amide compound. The method comprises the following steps: under the action of a catalyst, taking oxygen as an oxidant, and carrying out oxidative amidation reaction on an alpha-diazoketone compound shown in a chemical formula 2 and a cyclic secondary amine compound shown in a chemical formula 3 in an organic solvent to obtain the alpha-carbonyl amide compound shown in a chemical formula 1, wherein the formulas 1, 2 and 3 are also shown in the speification. According to the preparation method disclosed by the invention, the alpha-carbonyl amide compound is obtained by taking oxygen as the oxidizing agent and catalyzing alpha-diazoketone and cyclic secondary amine to be subjected to oxidative amidation reaction through cuprous iodide, the reaction condition is mild, the reaction time is short, and the byproduct of the reaction is only nitrogen, so that the method is an effective way for green and efficient preparation of the alpha-carbonyl amide compound.

Diversification of α-ketoamides: Via transamidation reactions with alkyl and benzyl amines at room temperature

A wide range of N-tosyl α-ketoamides underwent transamidation with various alkyl amines in the absence of a catalyst, base, or additive. On the other hand, transamidation in N-Boc α-ketoamides was achieved in the presence of Cs2CO3. The reactions proceede

Selective electrochemical oxidation of aromatic hydrocarbons and preparation of mono/multi-carbonyl compounds

A selective electrochemical oxidation was developed under mild condition. Various mono-carbonyl and multi-carbonyl compounds can be prepared from different aromatic hydrocarbons with moderate to excellent yield and selectivity by virtue of this electrochemical oxidation. The produced carbonyl compounds can be further transformed into α-ketoamides, homoallylic alcohols and oximes in a one-pot reaction. In particular, a series of α-ketoamides were prepared in a one-pot continuous electrolysis. Mechanistic studies showed that 2,2,2-trifluoroethan-1-ol (TFE) can interact with catalyst species and generate the corresponding hydrogen-bonding complex to enhance the electrochemical oxidation performance. [Figure not available: see fulltext.]

Cu(OAc)2 and acids promoted the oxidative cleavage of α-aminocarbonyl compounds with amines: efficient and selective synthesis of 2-t-amino-2-imino-carbonyl and 2-amino-2-oxocarbonyl

A novel and efficient method for the synthesis of 2-t-amino-2-imino-carbonyl (C) and 2-amino-2-oxocarbonyl (D) compounds has been discovered through a copper-promoted oxidating amidation reactions between α-amino -carbonyl compounds and amines. Promoted by the crucial copper species, perfect selectivity and good to excellent yields could be achieved. This transformation is achieved through C[sbnd]N bond oxidative cleavage and formation a novel C[sbnd]N bond. This reaction system has a broad reaction scope, providing a facile pathway for the α-functionalization of α-amino ketones.

Structure–activity relationships (SARs) of α- ketothioamides as inhibitors of phosphoglycerate dehydrogenase (PHGDH)

For many years now, targeting deregulation within cancer cells’ metabolism has appeared as a promising strategy for the development of more specific and efficient cancer treatments. Recently, numerous reports highlighted the crucial role of the serine synthetic pathway, and particularly of the phosphoglycerate dehydrogenase (PHGDH), the first enzyme of the pathway, to sustain cancer progression. Yet, because of very weak potencies usually in cell-based settings, the inhibitors reported so far failed to lay ground on the potential of this approach. In this paper, we report a structure–activity relationship study of a series of α-ketothioamides that we have recently identified. Interestingly, this study led to a deeper understanding of the structure–activity relationship (SAR) in this series and to the identification of new PHGDH inhibitors. The activity of the more potent compounds was confirmed by cellular thermal shift assays and in cell-based experiments. We hope that this research will eventually provide a new entry point, based on this promising chemical scaffold, for the development of therapeutic agents targeting PHGDH.

Cu-Catalyzed aerobic oxidative cleavage of C(sp3)–C(sp3) bond: Synthesis of α-ketoamides

A novel synthesis of α-ketoamides from Cu-catalyzed aerobic oxidative C(sp3)–C(sp3) bond cleavage of hydrocinnamaldehydes has been developed. Readily available and environmentally benign oxygen is used as the oxidant. This reaction avoids the use of noble metal catalysts or specialized oxidants, and chemoselectively yields α-ketoamide. Moreover, based on various control experiments, a reasonable mechanism is proposed.

Amine-Mediated Bond Cleavage in Oxidized Lignin Models

Introducing amines/ammonia into lignin cracking will allow novel bond cleavage pathways. Herein, a method of amines/ammonia-mediated bond cleavage in oxidized lignin β-O-4 models was studied using a copper catalyst at room temperature, demonstrating the effect of the amine source on the selectivity of products. For primary and secondary aliphatic amines, lignin ketone models underwent oxidative Cα?Cβ bond cleavage and Cα?N bond formation to generate aromatic amides. For ammonia, the competition between oxygen and ammonia determined the selectivity between Cα?N and Cβ?N bond formation, generating amides and α-keto amides, respectively. For tertiary amines, the lignin models underwent oxidative Cα?Cβ bond cleavage to benzoic acids. Control experiments indicated that amines act as nucleophiles attacking at the Cα or Cβ position of the oxidized β-O-4 linkage to be cleaved. This study represents a novel example that the breakage of oxidized lignin model can be regulated by amines with a copper catalyst.