A strategy for the synthesis of aryl alpha-ketoamides based upon the acylation of anions derived from cyanomethylamines followed by oxidative cleavage.
[reaction: see text] Cyanomethylamines, prepared by alkylation of amines with chloroacetonitrile, were deprotonated using NaHDMS in THF, reacted with heteroaryl or substitutedphenyl esters, and then oxidized by adding Clorox(TM) to afford aryl alpha-ketoamides in a single operation in good overall yields.
Yang
Zhong
Z
Department of Chemistry, The Bristol-Myers Squibb Pharmaceutical Research Institute, 5 Research Parkway, Wallingford, Connecticut 06492, USA.
Zhang
Zhongxing
Z
Meanwell
Nicholas A
NA
Kadow
John F
JF
Wang
Tao
T