A strategy for the synthesis of aryl alpha-ketoamides based upon the acylation of anions derived from cyanomethylamines followed by oxidative cleavage

Zhong Yang; Zhongxing Zhang; Nicholas A Meanwell; John F Kadow; Tao Wang

doi:10.1021/ol010297l

A strategy for the synthesis of aryl alpha-ketoamides based upon the acylation of anions derived from cyanomethylamines followed by oxidative cleavage

Org Lett. 2002 Apr 4;4(7):1103-5. doi: 10.1021/ol010297l.

Authors

Zhong Yang¹, Zhongxing Zhang, Nicholas A Meanwell, John F Kadow, Tao Wang

Affiliation

¹ Department of Chemistry, The Bristol-Myers Squibb Pharmaceutical Research Institute, 5 Research Parkway, Wallingford, Connecticut 06492, USA.

PMID: 11922793
DOI: 10.1021/ol010297l

Abstract

[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.