Iodine-mediated cascade cyclization of enediynes to iodinated benzo[a]carbazoles

J Org Chem. 2011 Dec 16;76(24):10269-74. doi: 10.1021/jo201795t. Epub 2011 Nov 10.

Abstract

Treatment of N,N-dimethyl 2-[2-(2-ethynylphenyl)ethynyl]anilines (1) with 1.2 equiv of iodine in CH(2)Cl(2) gave benzo[a]carbazoles (2) in good yields. Mechanistic studies showed this reaction must go through the haloindole (3) followed by iodonium ion catalyzed atom-transfer cyclization reaction to give the benzo[a]carbazoles.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aniline Compounds / chemistry*
  • Carbazoles / chemical synthesis*
  • Catalysis
  • Chemistry Techniques, Synthetic
  • Cyclization
  • Enediynes / chemistry*
  • Halogenation
  • Indoles / chemistry
  • Iodine*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure

Substances

  • Aniline Compounds
  • Carbazoles
  • Enediynes
  • Indoles
  • Iodine
  • aniline