5525-85-9Relevant academic research and scientific papers
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
Alkyl keto-amide, amidoxime compound thereof, and preparation and application of compound
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Paragraph 0036, (2019/01/23)
The invention relates to alkyl keto-amide, an amidoxime compound thereof, and preparation and application of the compound. The alkyl keto-amide compound and a derivative thereof can be applied to metal palladium catalyzed C-H bond fluoridation, better rea
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.
On Dien-Ketenes from o-Quinol-Acetates
Quinkert, Gerhard,Kleiner, Erna,Freitag, Bernd-Juergen,Glenneberg, Juergen,Billhardt, Uta-Maria,et al.
, p. 469 - 537 (2007/10/02)
A detailed picture of the photochemistry of o-quinol-acetates is presented. (RS)-6-Acetoxy-6-methyl-, (RS)-6-acetoxy-2,6-dimethyl-, (RS)-6-acetoxy-5,6-dimethyl-, (RS)-6-acetoxy-2,4,6-trimethyl-, (RS)-6-acetoxy-2,3,4,6-tetramethyl-, and (RS)-6-acetoxy-2,3,4,5,6-pentamethyl-2,4-cyclohexadien-1-ones serve as representative educts.There are two separate main photochemical routes conveniently designated as 1(?*,n) or 3(?*,?) tracks.The latter may also be attained by sensitization and leads to phenols.The former, by α-cleavage furnishes dien-ketens as indispensable phototransients.Photolysis of dien-ketens follows one or more of three reaction channels, each of which yields a particular type of photoproduct: heat-induced monocyclization affords 2,4-cyclohexadien-1-ones, heat-induced bicyclization stereoselectively furnishes bicyclohex-3-en-2-ones, and multi-step addition of protic nucleophiles stereoselectively gives 1,4-, 1,6- and/or 1,2-adducts.By X-ray analysis or NOE studies, the structure of isolated photoproducts is established.Conventional spectroscopy at low or flash spectroscopy at normal temperature yield information on the formation and decay of kinetically unstable intermediates.Photoproduct composition depends on the pattern of substitution of the educts, on the solvents, and on the nucleophiles that migth be present.Substituents primarily exert an influence upon the population of the various conformers of the dien-keten.Solvents affect the rate of the divers reaction paths competing for the phototransient.Nucleophiles play more than a trivial role when adducts are formed.With the detailed view of a dien-keten's role on hand, the photoproduct from a given o-quinol-acetate - or more general from a linear conjugated cyclohexadienone - is now predictable.
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-
Preparation and Reactions of 1-Lithio-oxy-1-lithio-amino-allene Derivatives
Adlington, Robert M.,Barrett, Anthony G. M.
, p. 65 - 67 (2007/10/02)
The title compounds Li+22CH=C=C(-O-)-N-R1>, prepared from secondary α-keto-amides via the Shapiro reaction, reacted at C-2 with aldehydes, acetone, and deuterium oxide; the products 2CH
