867299-41-0Relevant academic research and scientific papers
A Mild and Chemoselective Hydrosilylation of α-Keto Amides by Using a Cs2CO3/PMHS/2-MeTHF System
Kumar, Govindharaj,Muthukumar, Alagesan,Sekar, Govindasamy
, p. 4883 - 4890 (2017)
A Cs2CO3-catalyzed hydrosilylation reaction of α-keto amides that proceeds through the in situ formation of MeSiH3 has been developed by using inexpensive polymethylhydrosiloxane in 2-methyltetrahydrofuran (2-MeTHF) as the solvent. A wide range of aryl and alkyl α-keto amides, prepared from anilines and alkylamines, were subjected to the hydrosilylation conditions to afford α-hydroxy amides in moderate to excellent yields. This transition-metal-free protocol was applied to a chemoselective hydrosilylation, in which reduction occurred at the carbonyl of the α-keto amide functionality over that of the simple ketone, and further extended to a gram-scale protocol.
Potassium Phosphate-Catalyzed Chemoselective Reduction of α-Keto Amides: Route to Synthesize Passerini Adducts and 3-Phenyloxindoles
Muthukumar, Alagesan,Mamillapalli, N. Chary,Sekar, Govindasamy
, p. 643 - 652 (2016/02/27)
A chemoselective reduction of α-keto amides to biologically important α-hydroxy amides (mandelamides) by polymethylhydrosiloxane (PMHS) using 5 mol% potassium phosphate (K3PO4) as catalyst has been developed. This transition metal-free protocol discloses excellent chemoselectivity for the ketone reduction of α-keto amides in the presence of other reducible functionalities like ketone, nitro, halides, nitrile and amide. Also, the chemoselectively reduced α-hydroxy amide has been derivatized to isocyanide-free Passerini adducts. The N-alkyl-α-hydroxy amides have been successfully converted to 3-phenyloxindole derivatives by treatment with methanesulfonyl cholride and triethylamine.
Chemoselective reduction of α-keto amides using nickel catalysts
Mamillapalli, N. Chary,Sekar, Govidasamy
, p. 7881 - 7884 (2014/07/08)
Ni-catalysts are used for the first time to synthesize highly important α-hydroxy amides and β-amino alcohols from α-keto amides by chemoselective and complete reduction using hydrosilanes. Chemoselective complete reduction of α-keto amides in the presenc
