Abstract
Aromatic aldehydes react with amides of 1-methylindole-2-carboxylic acid under acid catalysis conditions to give 1-aryl-4-methyldihydropyrrolo[3,4-b]indol-3-ones. The intermediate 1-methyl-2-CONHR-3(α-X-benzyl)indoles, which are subsequently converted to the indicated cyclic compounds, were isolated. o-Acetyl derivatives were obtained by the action of acetic anhydride on derivatives of unsubstituted amides. Dihydropyrrolo[3,4-b] indol-3-ones were reduced by LiAlH4 to the corresponding dihydropyrrolo[3,4-b] indoles. A mechanism for the formation of dihydropyrrolo[3,4-b] indoles is proposed.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1516–1523, November, 1976.
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Kogan, N.A., Vlasova, M.I. Reaction of indoles with aldehydes. Synthesis of dihydropyrrolo[3,4-b]indoles. Chem Heterocycl Compd 12, 1249–1254 (1976). https://doi.org/10.1007/BF00470225
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DOI: https://doi.org/10.1007/BF00470225