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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A. V. Samet, V. N. Marshalkin, S. G. Zlotin, V. V. Semenov, A. A. Gakh, and A. C. Buchanan III, 218th ACS National Meeting, New Orleans, 1999, 47.
S. G. Zlotin, P. G. Kislitsin, A. V. Samet, E. A. Serebryakov, L. D. Konyushkin, V. V. Semenov, A. C. Buchanan III, and A. A. Gakh, J. Org. Chem., 2000, 65, 8430.
S. G. Zlotin, P. G. Kislitsin, A. I. Podgursky, A. V. Samet, V. V. Semenov, A. C. Buchanan III, and A. A. Gakh, J. Org. Chem., 2000, 65, 8439.
N. B. Chernysheva, A. V. Samet, V. N. Marshalkin, V. A. Polukeev, and V. V. Semenov, Mendeleev Commun., 2001, 109.
A. V. Samet, E. P. Zakharov, V. V. Semenov, A. A. Gakh, and A. C. Buchanan III, Synth. Commun., 2001, 31, 1441.
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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