Efficient synthesis of α- and δ-carbolines by sequential Pd-catalyzed site-selective C-C and twofold C-N coupling reactions

Org Biomol Chem. 2015 Feb 7;13(5):1375-86. doi: 10.1039/c4ob02226b.

Abstract

Two concise and efficient approaches were developed for the synthesis of α- and δ-carboline derivatives. The success of the synthesis relies on site-selective Suzuki-Miyaura reactions of 1-chloro-2-bromopyridine or 2,3-dibromopyridine with 2-bromophenylboronic acid and subsequent cyclization with amines which proceeds by twofold Pd-catalyzed C-N coupling reactions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boronic Acids / chemistry
  • Carbolines / chemical synthesis*
  • Carbolines / chemistry*
  • Carbon / chemistry*
  • Catalysis
  • Chemistry Techniques, Synthetic
  • Cyclization
  • Models, Molecular
  • Molecular Conformation
  • Nitrogen / chemistry*
  • Palladium / chemistry*
  • Pyridines / chemistry
  • Substrate Specificity

Substances

  • Boronic Acids
  • Carbolines
  • Pyridines
  • Palladium
  • Carbon
  • Nitrogen