Diverse tandem cyclization reactions of o-cyanoanilines and diaryliodonium salts with copper catalyst for the construction of quinazolinimine and acridine scaffolds

Org Lett. 2014 Dec 5;16(23):6228-31. doi: 10.1021/ol503156g. Epub 2014 Nov 24.

Abstract

Two cyclization modes are realized to produce different nitrogen-containing heterocycles, i.e., quinazolin-4(3H)-imines and acridines by assembling o-cyanoanilines and diaryliodonium salts via tandem reaction pathways.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acridines / chemical synthesis*
  • Acridines / chemistry
  • Aniline Compounds / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Cyclization
  • Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
  • Heterocyclic Compounds, 4 or More Rings / chemistry
  • Imines / chemical synthesis*
  • Imines / chemistry
  • Mesylates / chemistry
  • Molecular Structure
  • Nitrogen / chemistry
  • Onium Compounds / chemical synthesis*
  • Onium Compounds / chemistry
  • Quinazolines / chemistry*
  • Salts

Substances

  • Acridines
  • Aniline Compounds
  • Heterocyclic Compounds, 4 or More Rings
  • Imines
  • Mesylates
  • Onium Compounds
  • Quinazolines
  • Salts
  • Copper
  • trifluoromethanesulfonic acid
  • Nitrogen