title: Convenient syntheses of benzo-fluorinated dibenz[b,f]azepines: rearrangements of isatins, acridines, and indoles.
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.
authors.affiliation: Robert Robinson Laboratories, Department of Chemistry, University of Liverpool, Liverpool L69 7ZD, UK.
authors.forename: Emma-Claire
authors.initials: EC
authors.lastname: Elliott
authors.forename: Elizabeth R
authors.initials: ER
authors.lastname: Bowkett
authors.forename: James L
authors.initials: JL
authors.lastname: Maggs
authors.forename: John
authors.initials: J
authors.lastname: Bacsa
authors.forename: B Kevin
authors.initials: BK
authors.lastname: Park
authors.forename: Sophie L
authors.initials: SL
authors.lastname: Regan
authors.forename: Paul M
authors.initials: PM
authors.lastname: O'Neill
authors.forename: Andrew V
authors.initials: AV
authors.lastname: Stachulski
mesh_terms: D000166:Acridines / Q000737:chemistry*; D000927:Anticonvulsants / Q000138:chemical synthesis / Q000737:chemistry; D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry; D002220:Carbamazepine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D007510:Isatin / Q000031:analogs & derivatives* / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D000166:Acridines; D000927:Anticonvulsants; D001381:Azepines; D006845:Hydrocarbons, Fluorinated; D007211:Indoles; D002220:Carbamazepine; D007510:Isatin