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Convenient Syntheses of Benzo-Fluorinated Dibenz[b,f]azepines: Rearrangements of Isatins, Acridines, and Indoles

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journal contribution
posted on 21.10.2011, 00:00 by Emma-Claire Elliott, Elizabeth R. Bowkett, James L. Maggs, John Bacsa, B. Kevin Park, Sophie L. Regan, Paul M. O’Neill, Andrew V. Stachulski
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.