New chemistry with old functional groups: on the reaction of isonitriles with carboxylic acids--a route to various amide types

J Am Chem Soc. 2008 Apr 23;130(16):5446-8. doi: 10.1021/ja800612r. Epub 2008 Mar 28.

Abstract

Thermolysis of isonitriles with carboxylic acids provides, in one step, N-formyl imides (see, for example, 8 + 19 --> 21). The resultant N-formyl group can be converted to N-H, NCH2OH, or NCH3. This chemistry allows for a new route for synthesizing beta-N (asparagine)-linked glycosyl amino acids.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Amides / chemical synthesis*
  • Asparagine / analogs & derivatives
  • Asparagine / chemical synthesis*
  • Carboxylic Acids / chemistry*
  • Glycopeptides / chemical synthesis*
  • Imides / chemistry
  • Models, Chemical
  • Nitriles / chemistry*

Substances

  • Amides
  • Carboxylic Acids
  • Glycopeptides
  • Imides
  • Nitriles
  • Asparagine