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Issue 48, 2013
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Convenient syntheses of halo-dibenz[b,f]azepines and carbamazepine analogues via N-arylindoles

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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.

Graphical abstract: Convenient syntheses of halo-dibenz[b,f]azepines and carbamazepine analogues via N-arylindoles

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Publication details

The article was received on 18 Jun 2013, accepted on 22 Oct 2013 and first published on 28 Oct 2013


Article type: Paper
DOI: 10.1039/C3OB41252K
Citation: Org. Biomol. Chem., 2013,11, 8426-8434
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    Convenient syntheses of halo-dibenz[b,f]azepines and carbamazepine analogues via N-arylindoles

    E. Elliott, J. L. Maggs, B. K. Park, P. M. O'Neill and A. V. Stachulski, Org. Biomol. Chem., 2013, 11, 8426
    DOI: 10.1039/C3OB41252K

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