5525-85-9Relevant articles and documents
Synthesis of aliphatic α-ketoamides from α-substituted methyl ketones: Via a Cu-catalyzed aerobic oxidative amidation
Cha, Hyojin,Chai, Jin Young,Chi, Dae Yoon,Kim, Hyeong Baik
supporting information, p. 4320 - 4326 (2021/05/31)
α-Ketoamides are an important key functional group and have been used as versatile and valuable intermediates and synthons in a variety of functional group transformations. Synthetic methods for making aryl α-ketoamides as drug candidates have been greatly improved through metal-catalyzed aerobic oxidative amidations. However, the preparation of alkyl α-ketoamides through metal-catalyzed aerobic oxidative amidations has not been reported because generating α-ketoamides from aliphatic ketones with two α-carbons theoretically provides two distinct α-ketoamides. Our strategy is to activate the α-carbon by introducing an N-substituent at one of the two α-positions. The key to this strategy is how heterocyclic compounds such as triazoles and imidazoles affect the selectivity of the synthesis of the alkyl α-ketoamides. From this basic concept, and by optimizing the reaction and elucidating the mechanism of the synthesis of aryl α-ketoamides via a copper-catalyzed aerobic oxidative amidation, we prepared fourteen aliphatic α-ketoamides in high yields (48-84%). This journal is
Catalyst-free three-component synthesis of highly functionalized 2,3-dihydropyrroles
Wang, Dong,Li, Linna,Feng, Hairong,Sun, Hua,Almeida-Veloso, Fabrice,Charavin, Marine,Yu, Peng,Désaubry, Laurent
supporting information, p. 2775 - 2780 (2018/06/27)
An efficient synthesis of fully substituted 2,3-dihydropyrroles has been achieved in one step through the three-component reaction of amines, aromatic aldehydes and α-ketoamides. This atom-economical and catalyst-free reaction is highly stereoselective and generates underexplored heterocycles in a single step. These compounds were examined in an enzymatic assay that led to the identification of potent α-glucosidase inhibitors, thereby demonstrating the utility of this novel methodology in medicinal chemistry.
Synthesis of 3-Methyleneazetidin-2-one Derivatives from α-Keto-amides
Adlington, Robert M.,Barrett, Anthony G.M.,Quayle, Peter,Walker, Andrew,Betts, Michael J.
, p. 605 - 612 (2007/10/02)
Several α-methyleneazetidin-2-one derivatives (CH2=CCONR1CHR2, R1 = cyclohexyl, PhCH2; R2 = H, Me, Et, Prn, etc.) were prepared from the 2-(2,4,6-tri-isopropylbenzenesulphonylhydrazones) of primary α-
