Synthesis of fused 1-aminoindole polycycles by a sequence of palladium-catalyzed N–H and C(sp2)–H arylations

J Org Chem. 2015 Jan 16;80(2):751-61. doi: 10.1021/jo502137y.

Abstract

An efficient Pd-catalyzed selective intramolecular arylation of functionalized N,N′-substituted 1-aminoindoles has been reported. In all cases, the reactions take place rapidly in DMA and efficiently proceed in the presence of a Pd(OAc)2/Dpephos catalytic system, furnishing the fused indolo[2,1-a]phthalazines in high yields. Additionally, the one-pot double C–H arylation at positions C-2 and C-3 of N,N′-substituted 1-aminoindoles is effective and leads to unknown complex scaffolds of biological interest.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cyclization
  • Hydrogen Bonding
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Molecular Structure
  • Palladium / chemistry*

Substances

  • Indoles
  • Palladium
  • 5-aminoindole