One-pot synthesis of ureas from Boc-protected amines

J Org Chem. 2014 May 16;79(10):4477-83. doi: 10.1021/jo500492x. Epub 2014 Apr 30.

Abstract

A practical one-pot synthesis of ureas is described. Boc-protected amines can be transformed into nonsymmetrical and symmetrical disubstituted and trisubstituted ureas utilizing 2-chloropyridine and trifluoromethanesulfonyl anhydride for the in situ generation of an isocyanate, which reacts with an amine. A variety of amines can be employed successfully, leading to high yields of isolated ureas.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry*
  • Mesylates / chemistry*
  • Molecular Structure
  • Pyridines / chemistry*
  • Urea / analogs & derivatives
  • Urea / chemical synthesis*
  • Urea / chemistry

Substances

  • Amines
  • Mesylates
  • Pyridines
  • 2-chloropyridine
  • Urea
  • trifluoromethanesulfonic acid