Complementary heterogeneous/homogeneous protocols for the synthesis of densely functionalized benzo[d]sultams: C-C bond formation by intramolecular nucleophilic aromatic fluorine displacement

J Org Chem. 2008 Sep 5;73(17):6686-90. doi: 10.1021/jo800930g. Epub 2008 Aug 8.

Abstract

Polyfunctionalized benzo[d]sultams 7 and 8, which contain an alpha-amino acid unit, have been synthesized from the corresponding open chain (pentafluorobenzene)sulfonamides 4 by complementary solid-liquid phase transfer catalysis (SL-PTC) and homogeneous protocols. The cyclization step proceeds through the intramolecular nucleophilic displacement of an aromatic fluorine atom.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetonitriles / chemistry
  • Amino Acids / chemistry
  • Carbon / chemistry*
  • Catalysis
  • Combinatorial Chemistry Techniques / methods*
  • Cyclization
  • Fluorine / chemistry
  • Fluorobenzenes / chemistry*
  • Hydrocarbons, Iodinated / chemistry
  • Models, Chemical
  • Sulfonamides / chemical synthesis*

Substances

  • Acetonitriles
  • Amino Acids
  • Fluorobenzenes
  • Hydrocarbons, Iodinated
  • Sulfonamides
  • beta-sultam
  • Fluorine
  • Carbon
  • methyl iodide