1267642-47-6Relevant 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
, 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
Friedel-Crafts Hydroxyalkylation of Indoles with α-Keto Amides using Reusable K3PO4/ nBu4NBr Catalytic System in Water
Muthukumar, Alagesan,Sekar, Govindasamy
, p. 8827 - 8839 (2018/08/03)
A mild and operationally simple Friedel-Crafts hydroxyalkylation of indoles with α-keto amides was developed for the first time by using catalytic amount of K3PO4 and nBu4NBr in water as solvent through a solid-liquid inte
Visible-light initiated copper(i)-catalysed oxidative C-N coupling of anilines with terminal alkynes: One-step synthesis of α-ketoamides
Sagadevan, Arunachalam,Ragupathi, Ayyakkannu,Lin, Chun-Cheng,Hwu, Jih Ru,Hwang, Kuo Chu
supporting information, p. 1113 - 1119 (2015/03/04)
Development of C-N coupling processes is fundamentally important and challenging for the synthesis of biologically active molecules and drugs. Herein, we report a highly atom efficient green process for the synthesis of α-ketoamides via visible-light induced copper(i) chloride catalysed direct oxidative Csp-N coupling reactions using commercially available alkynes and anilines at room temperature without the use of hazardous chemicals and harsh reaction conditions. Forty-seven examples are presented using a broad range of substrates including electron deficient anilines and various terminal alkynes. The current photochemical process is able to achieve epoxide hydrolase inhibitors in one step with high yield (92-95%). This transformation is highly efficient and highly selective for the synthesis of α-ketoamides. This journal is
