Synthesis of α-Ketoamides from a Carbamoylsilane and Acid Chlorides

Abstract

Treatment of acid chlorides with a carbamoylsilane affords alpha-ketoamides. In some instances, in situ reaction of additional carbamoylsilane with these products yielded alpha-organyl-alpha-siloxymalonamides.

CuI‐Mediated α‐Ketoacylation of Sulfoximines under Solvent‐Free Conditions

“…Based on mechanistic precedent [8][9][10][11]13,16] and our preliminary studies, we propose an unprecedented double catalytic cycle involving elemental iodine and copper for the formation of 1 in Figure 1. Thus, I 2 and Cu II are generated in situ by oxidative reaction of iodine anion, CuI with oxidant (DTBP).…”

“…Typically, α-keto amides have been synthesized by α-ketoacylation of the corresponding amines with acyl halides or carboxylic acids. However, these methods either require uncommon substrates such as unstable α-ketoacids, [7] special α-ketoacyl halides [8] and so forth, or suffer from stringent experimental conditions. Recently, some novel approaches for overcoming these drawbacks have been developed that make use of a dual C-H/N-H activation pathway from two nucleophilic reagents.…”

SeO2 mediated efficient synthesis of amides and α-ketoamides of secondary amines with wide substrate scope

“…1 pharmaceuticals (rapamycin, enzyme inhibitors) and agrochemicals (FK506). 2-4 α-Ketoamides are synthesized from diverse substrates such as methyl-ketones, 5-10 aldehydes/arylglyox-als, [11][12][13][14][15][16] -ketoacids, [17][18][19][20] terminal alkynes, [21][22][23][24] cyanamides, 25 carbamoyl stannane/ silane with acid chlorides, [26][27][28] addition of aroyl to aryl-acetamides, 29 2,2-dibromo-1-aryl ethanones 30 and double carbonylation of aryl iodides. [31][32][33] Usually in these oxidative amidation, a co-oxidant is required.…”

α-Ketoamino acid ester derivatives as promising MAO inhibitors

“…[15][16][17][18] In parallel, their application in medicinal chemistry has fueled the development of several synthetic methods. [19][20][21][22][23][24][25][26][27][28][29][30] The synthesis of an a-ketoamide fragment could be achieved by the ring opening of N-acetylisatin 1 by attacking of an amine at C2-carbonyl group of N-acetylisatin. [31][32][33][34][35][36][37][38][39] Recently, Cheah et al 39 reported the synthesis of N-glyoxylamide peptide mimics from the reaction of N-acetylisatin with a-amino esters.…”