Direct imine acylation: rapid access to diverse heterocyclic scaffolds

Org Lett. 2013 Jan 18;15(2):258-61. doi: 10.1021/ol303073b. Epub 2012 Dec 24.

Abstract

A simple and efficient procedure to prepare a range of diverse heterocycles by the direct acylation of imines using a variety of functionalized benzoic acids is described. The methodology features a novel method for N-acyliminium ion generation followed by in situ intramolecular trapping by oxygen-, nitrogen-, sulfur- and carbon-based nucleophiles. Preliminary mechanistic studies, using ReactIR, are also reported.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acylation
  • Combinatorial Chemistry Techniques
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Imines / chemistry*
  • Indole Alkaloids / chemical synthesis*
  • Indole Alkaloids / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Structure

Substances

  • Heterocyclic Compounds
  • Imines
  • Indole Alkaloids
  • evodamine