64201-19-0

Upstream product

• 611-73-4 Benzoylformic acid 
• 91-66-7 N,N-diethylaniline 
• 25726-04-9 phenylglyoxylyl chloride 
• 103-69-5 N-ethyl-N-phenylamine 
• 613-97-8 N-methyl-N-ethylaniline 
• 1074-12-0 phenylglyoxal hydrate 
• 122-78-1 phenylacetaldehyde 
• 64-19-7 acetic acid 

Downstream Products

• 5554-43-8 N-ethyl-benzilanilide 
• 64201-08-7 2-methyl-3,5-diphenyl-oxazolidin-4-one 
• 64200-99-3 3-hydroxy-4-methyl-1,3-diphenyl-azetidin-2-one 
• 138835-13-9 N-ethyl-2-hydroxy-N,2-diphenylacetamide 
• 138835-15-1 C₁₆H₁₄⁽²⁾HNO₂ 
• 4410-33-7 N-phenyl-2-hydroxy-4-phenylacetamide 
• 4358-87-6 (RS)-methyl mandelate 

Relevant academic research and scientific papers

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

Photoredox-Catalyzed Tandem Demethylation of N,N-Dimethyl Anilines Followed by Amidation with α-Keto or Alkynyl Carboxylic Acids

We report herein, a biomimetic approach for highly selective monodemethylation of N,N-dimethyl anilines to generate secondary amines and subsequent coupling with α-ketocarboxylic acids or alkynyl carboxylic acids to form α-ketoamides or alkynamides respectively under visible light photoredox catalyst in a single operation. From the deuterium-labeling experiment, it was probed that demethylation is the slowest step in this tandem process. Whereas, control experiments and spectroscopic studies revealed that photoredox catalyst is also involved in the subsequent amidation step. The reaction proceeds smoothly at room temperature providing moderate to excellent yield of the coupling products. The amides have also been converted to a series of biologically active spiro compounds. (Figure presented.).

Potassium Phosphate-Catalyzed Chemoselective Reduction of α-Keto Amides: Route to Synthesize Passerini Adducts and 3-Phenyloxindoles

A chemoselective reduction of α-keto amides to biologically important α-hydroxy amides (mandelamides) by polymethylhydrosiloxane (PMHS) using 5 mol% potassium phosphate (K3PO4) as catalyst has been developed. This transition metal-free protocol discloses excellent chemoselectivity for the ketone reduction of α-keto amides in the presence of other reducible functionalities like ketone, nitro, halides, nitrile and amide. Also, the chemoselectively reduced α-hydroxy amide has been derivatized to isocyanide-free Passerini adducts. The N-alkyl-α-hydroxy amides have been successfully converted to 3-phenyloxindole derivatives by treatment with methanesulfonyl cholride and triethylamine.

Silver-catalyzed amidation of benzoylformic acids with tertiary amines via selective carbon-nitrogen bond cleavage

A novel approach towards the synthesis of α-ketoamides using tertiary amines as nitrogen group sources via C-N bond cleavage has been developed. In the presence of Ag2CO3 and K2S 2O8, α-keto acids reacted with tertiary amines to afford the corresponding α-ketoamides in good yields. The Royal Society of Chemistry 2013.

Copper-catalyzed aerobic oxidative cross-dehydrogenative coupling of amine and α-carbonyl aldehyde: A practical and efficient approach to α-ketoamides with wide substrate scope

A copper-catalyzed aerobic oxidative cross-dehydrogenative coupling (CDC) of amine with α-carbonyl aldehyde has been developed. Many types of amines are tolerant in this transformation leading to various α-ketoamides compounds. Wide substrate scope, CDC strategy and using air as oxidant make this transformation highly efficient and practical. Molecular oxygen acts not only as the oxidant, but also as an initiator to trigger this catalytic process. Furthermore, mechanism studies show that carbonyl group of α-carbonyl aldehyde plays a role as the directing group to facilitate this chemical process.

Copper-catalyzed aerobic oxidative coupling of aryl acetaldehydes with anilines leading to α-ketoamides

Efficient and practical: The title reaction provides an efficient route to α-ketoamides compounds, which are ubiquitous structural units in a number of biologically active compounds. N-substituted anilines are suitable substrates for this transformation.

Cyclization reactions of methylthioacetanilides

The cyclization reactions of methylthioacetanilides mediated by manganese(III) acetate and/or copper(II) acetate are described. Indolinones and indolinediones can be produced effectively via a 5-membered ring cyclization of methylthioacetanilides. The product distributions are highly dependent on the reaction conditions. In most cases, the electronic effect of the substituents on the aryl ring was found to significantly affect the yields of cyclization products. This cyclization reaction proceeded faster with manganese(III) acetate/copper(II) acetate.