One-pot synthesis of pyrimido[1,6-a]indol-1(2H)-one derivatives by a nucleophilic addition/Cu-catalyzed N-arylation/Pd-catalyzed C-H activation sequential process

Org Lett. 2010 Jul 2;12(13):3034-7. doi: 10.1021/ol101041e.

Abstract

A novel and convenient one-pot synthesis of pyrimido[1,6-a]indol-1(2H)-one derivatives through a nucleophilic addition/Cu-catalyzed N-arylation/Pd-catalyzed C-H activation sequential process is described. The reaction of easily prepared ortho-gem-dibromovinyl isocyanates with N-alkyl-anilines gave the desired indole derivatives in moderate to good yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aniline Compounds / chemistry
  • Catalysis
  • Copper / chemistry*
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Iodides / chemistry*
  • Isocyanates / chemistry
  • Molecular Structure
  • Palladium / chemistry*
  • Pyrimidines / chemical synthesis*
  • Pyrimidines / chemistry
  • Stereoisomerism

Substances

  • Aniline Compounds
  • Indoles
  • Iodides
  • Isocyanates
  • Pyrimidines
  • pyrimido(1,6-a)indol-1(2H)-one
  • Palladium
  • Copper
  • cuprous iodide
  • aniline