N-Methylimidazole-catalyzed synthesis of carbamates from hydroxamic acids via the Lossen rearrangement

Org Lett. 2013 Feb 1;15(3):602-5. doi: 10.1021/ol303424b. Epub 2013 Jan 17.

Abstract

An efficient, one-pot, N-methylimidazole (NMI) accelerated synthesis of aromatic and aliphatic carbamates via the Lossen rearrangement is reported. NMI is a catalyst for the conversion of isocyanate intermediates to the carbamates. Moreover, the utility of arylsulfonyl chloride in combination with NMI minimizes the formation of often-observed hydroxamate-isocyanate dimers during the sequence. Under the present conditions, lowering of temperatures is also possible, enabling a mild protocol.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbamates / chemical synthesis*
  • Carbamates / chemistry
  • Catalysis
  • Chlorides
  • Combinatorial Chemistry Techniques
  • Esters
  • Hydroxamic Acids / chemistry*
  • Imidazoles / chemistry*
  • Molecular Structure
  • Polymers

Substances

  • Carbamates
  • Chlorides
  • Esters
  • Hydroxamic Acids
  • Imidazoles
  • Polymers
  • 1-methylimidazole