title: Convenient syntheses of halo-dibenz[b,f]azepines and carbamazepine analogues via N-arylindoles.
abstract: The dibenz[b,f]azepine heterocyclic system and related molecules with a single 10,11-bond are important templates for well-prescribed drug molecules, notably carbamazepine (anticonvulsant), clomipramine and imipramine (antidepressants). We synthesised a range of halogenated carbamazepine analogues, in connection with metabolic and immunological studies, as probes for structure-metabolism and hypersensitive effects and have published on their metabolic behaviour. While a number of synthetic routes to such analogues are possible, we naturally sought short and efficient methods for our target compounds. In the following report we present an effective two-step synthesis of a range of dibenz[b,f]azepines from appropriate indoles via N-arylation, then acid-catalysed rearrangement, with a critical analysis of other approaches. We showed earlier that this route was effective for fluoro analogues and here present a broader review of its scope. The 5-(carboxamido) side chain of carbamazepine may be added in various ways, affording overall a convenient access to drug molecules.
authors.affiliation: Department of Chemistry, University of Liverpool, Liverpool L69 7ZD, UK. stachuls@liv.ac.uk.
authors.forename: Emma-Claire
authors.initials: EC
authors.lastname: Elliott
authors.forename: James L
authors.initials: JL
authors.lastname: Maggs
authors.forename: B Kevin
authors.initials: BK
authors.lastname: Park
authors.forename: Paul M
authors.initials: PM
authors.lastname: O'Neill
authors.forename: Andrew V
authors.initials: AV
authors.lastname: Stachulski
mesh_terms: D000927:Anticonvulsants / Q000138:chemical synthesis / Q000737:chemistry; D002220:Carbamazepine / Q000031:analogs & derivatives / Q000138:chemical synthesis; D002384:Catalysis; D003984:Dibenzazepines / Q000138:chemical synthesis* / Q000737:chemistry; D054879:Halogenation; D007211:Indoles / Q000737:chemistry*
chemical_list: D000927:Anticonvulsants; D003984:Dibenzazepines; D007211:Indoles; D002220:Carbamazepine