Convenient syntheses of benzo-fluorinated dibenz[b,f]azepines: rearrangements of isatins, acridines, and indoles

Org Lett. 2011 Oct 21;13(20):5592-5. doi: 10.1021/ol202318w. Epub 2011 Sep 22.

Abstract

Efficient procedures for the synthesis of benzo-fluorinated dibenz[b,f]azepines (iminostilbenes) from fluorinated isatins or indoles using a number of ring-expansion reactions are described. A range of mono- and difluorinated analogues is accessible, and the syntheses can deliver gram quantities of the final products, which are precursors of fluoro analogues of the important anticonvulsant carbamazepine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acridines / chemistry*
  • Anticonvulsants / chemical synthesis
  • Anticonvulsants / chemistry
  • Azepines / chemical synthesis*
  • Azepines / chemistry
  • Carbamazepine / analogs & derivatives
  • Carbamazepine / chemical synthesis
  • Carbamazepine / chemistry
  • Catalysis
  • Hydrocarbons, Fluorinated / chemical synthesis*
  • Hydrocarbons, Fluorinated / chemistry*
  • Indoles / chemistry*
  • Isatin / analogs & derivatives*
  • Isatin / chemistry*
  • Molecular Structure

Substances

  • Acridines
  • Anticonvulsants
  • Azepines
  • Hydrocarbons, Fluorinated
  • Indoles
  • Carbamazepine
  • Isatin