Copper-catalyzed synthesis of medium- and large-sized nitrogen heterocycles via N-arylation of phosphoramidates and carbamates

Org Lett. 2005 Oct 13;7(21):4781-4. doi: 10.1021/ol052126c.

Abstract

[reaction: see text] We have developed an efficient method for the preparation of medium- and large-sized nitrogen heterocycles via copper-catalyzed intramolecular N-arylation of phosphoramidates and carbamates. Introduction of the phosphoryl group or tert-butoxycarbonyl at N-termini can improve intramolecular cyclization under copper catalysis, and the phosphoryl and tert-butoxycarbonyl can easily be removed under the mild conditions; thus, the convenient and efficient method is suitable for the preparation of medium- and large-sized nitrogen heterocycles.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry*
  • Benzene Derivatives / chemical synthesis*
  • Benzene Derivatives / chemistry
  • Carbamates / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Cyclization
  • Heterocyclic Compounds, 2-Ring / chemical synthesis*
  • Heterocyclic Compounds, 2-Ring / chemistry
  • Molecular Structure
  • Nitrogen / chemistry*
  • Phosphoric Acids / chemistry*

Substances

  • Amides
  • Benzene Derivatives
  • Carbamates
  • Heterocyclic Compounds, 2-Ring
  • Phosphoric Acids
  • Copper
  • phosphoramidic acid
  • Nitrogen