69374-78-3

Upstream product

• 7163-50-0 (4-methylphenyl)(oxo)acetic acid 
• 37852-42-9 ethyl 2-p-tolylacetimidate hydrochloride 
• 2947-61-7 (4-methylphenyl)acetonitrile 
• 17263-64-8 2-diazo-1-(4-methylphenyl)ethanone 
• 14271-73-9 4-methylbenzoyl cyanide 
• 122-00-9 para-methylacetophenone 
• 105457-91-8 2-oxo-2-(p-tolyl)acetyl chloride 
• 5524-56-1 ethyl 2-p-tolyl-2-oxoacetate 

Downstream Products

• 18584-26-4 2-hydroxy-2-p-tolylacetamide 
• 677743-35-0 (R)-2-hydroxy-2-p-tolylacetamide 

Relevant academic research and scientific papers

Oxidative Coupling of Diazo and NH4I: A Route to Primary Oxamates and α-Ketoamides

A simple and efficient method has been developed for the preparation of primary oxamates and α-ketoamides through the oxidative coupling of diazo compounds and NH4I. Under the optimized reaction conditions, a range of diazoesters and α-diazoketones was explored, and the corresponding products were obtained in moderate to good yields. This protocol is metal-free, is performed under mild conditions, has a wide substrate scope, and offers operational simplicity.

Green preparation method of alpha-keto-amide

The invention discloses a method for preparing alpha-keto-amide. The method takes alpha-diazo-ketones compound and ammonium iodide as reaction substrates, under the condition of transition metal-freeand alkali-free, takes tert-butyl hydroperoxide (TBHP) a

UV Assisted High-Efficient Synthesis of α-Ketoamides using Air Promoted by A Non-Metal Catalyst in Aqueous Solution

Presented here is the first example of UV (λ=210 nm) promoted procedure proceeding in aqueous media at room temperature using ambient air as the oxidant for efficient synthesis of an array of α-ketoamides of all types using a non-metal catalyst N-iodosuccinimide with a loading of 20 mol%. With UV, oxygen in the air was efficiently utilized as the green oxidant, some control experiments were carried out and a plausible mechanism was proposed, disclosing that in aqueous solution, the oxidation process was actually triggered by dioxygen radical anion (O2.?), while not molecular oxygen. A variety of secondary amines and primary amines as well as ammonia were employed as the amine moieties, and the desired product primary-, secondary-, and tertiary α-ketoamides were afforded in good to excellent yields of up to 96 %.

nBu4NI-Mediated oxidation of methyl ketones to α-ketoamides: using ammonium, primary and secondary amine-salt as an amine moiety

Presented here is the first example of synthesizing an array of primary-, secondary-, and tertiary-α-ketoamides with a non-metal catalyst nBu4NI from methyl ketones and inexpensive readily available amine/ammonium salts; the reactions proceeded smoothly under mild conditions, TBHP was used as an oxidant and the corresponding α-ketoamides were afforded in moderate to excellent yields.

Copper(II)-Mediated Aerobic Oxidation of Benzylimidates: Synthesis of Primary α-Ketoamides

A simple and straightforward method for the synthesis of primary α-ketoamides has been discovered. The reaction represents the first example of benzylimidates directly converting to primary α-ketoamides by using sustainable molecular oxygen as an oxidant. This reaction proceeds in the presence of copper(II) salt via cleavage of benzylic C-H and C-O bonds of the benzylimidates with liberation of alcohols as the only byproduct. A wide substrate scope, operationally mild conditions, the use of single substrates, and a reaction scaled up to grams make this strategy very attractive and practical. Furthermore, mechanistic studies illustrate that the imidate group adjacent to the benzylic position plays crucial role in facilitating this chemical process.

Selective hydration of nitriles to amides catalysed by PCP pincer supported nickel(ii) complexes

The (PCP)Ni-OH complexes 2R (R = iPr, tBu, Cy) are effective catalyst precursors for the selective hydration of nitriles to the corresponding amides under relatively mild conditions (80 °C) and low catalyst loadings (0.05-0.5%). Substrate scope includes aliphatic, vinylic and aromatic nitriles, but substrates with protic groups poison the catalyst abruptly. The catalysts are effective because the electron rich nature of the PCP ligands and their steric bulk renders the hydroxo group labile.

Formamidine hydrochloride as an amino surrogate: I2-catalyzed oxidative amidation of aryl methyl ketones leading to free (N-H) α-ketoamides

A highly efficient molecular iodine catalyzed oxidative amidation of aryl methyl ketones with formamidine hydrochloride has been developed. This reaction represents a novel strategy for the synthesis of free (N-H) α-ketoamides. Based on the experimental r

A novel approach for the one-pot preparation of α-ketoamides by anodic oxidation

The direct oxidative synthesis of α-ketoamides via anodic oxidation was developed by using dioxygen as a reactant under mild conditions. This methodology has a broad substrate scope (aromatic amines, aliphatic amines and ammonium acetate) and opens up an interesting and attractive avenue for the synthesis of α-ketoamide derivatives.

Biocatalytic reduction of α-keto amides to (R)-α-hydroxy amides using Candida parapsilosis ATCC 7330

Biocatalytic reduction of primary and secondary α-keto amides was accomplished using whole cells of Candida parapsilosis ATCC 7330. The primary (R)-α-hydroxy amides were obtained in good enantiomeric excess (up to 94%) and conversion (88-99%) as compared to the secondary (R)-α-hydroxy amides.