Amination of heterocyclic compounds with o-benzoylhydroxylamine derivatives

Org Lett. 2007 Sep 13;9(19):3821-4. doi: 10.1021/ol701730r. Epub 2007 Aug 24.

Abstract

The N-amination of heterocyclic compounds 1a-k with O-benzoylhydroxylamine derivatives 5 was developed and demonstrated to be a superior alternative to existing N-amination methods. A structure-reactivity relationship study was performed on variously substituted O-benzoylhydroxylamine derivatives, leading to the discovery of the novel and more efficient aminating reagents 5h and 5i.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amination
  • Anions
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Hydrolysis
  • Hydroxylamines / chemistry*
  • Isomerism
  • Kinetics
  • Molecular Structure
  • Pyrroles / chemistry
  • Triazines / chemistry
  • Water / chemistry

Substances

  • Anions
  • Heterocyclic Compounds
  • Hydroxylamines
  • Pyrroles
  • Triazines
  • Water
  • O-benzoylhydroxylamine