The reduction of the nitro-derivatives (4a–c) with iron–acetic acid leads to the pyrrolo[3,2-b]indoles (7a–c). This unusual indolization, in which displacement of the heterocycle amino-group occurs, is regarded as a nucleophilic attack by the 2-aminophenyl group on the pyrrole ring, and is an interesting example of intramolecular nucleophilic substitution in the pyrrole series.
E. Aiello, G. Dattolo and G. Cirrincione, J. Chem. Soc., Perkin Trans. 1, 1981, 1 DOI: 10.1039/P19810000001
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