Abstract
4,6-Dinitro-1-tosylindoline prepared from trinitrotoluene undergoes base-catalyzed condensation with aromatic aldehydes. With salicylaldehyde and 2-hydroxynaphthalene-1-carbaldehyde, the condensation is accompanied by intramolecular nucleophilic substitution for one of the nitro groups to give benzo- and naphthooxepino[4,3,2-cd]indoles, respectively.
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Yamskov, A.N., Samet, A.V. & Semenov, V.V. Synthesis of fused indoles from 2,4,6-trinitrotoluene. Russian Chemical Bulletin 52, 759–760 (2003). https://doi.org/10.1023/A:1023999915911
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DOI: https://doi.org/10.1023/A:1023999915911