Reaction of indoles with aldehydes. Synthesis of dihydropyrrolo[3,4-b]indoles |
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Authors: | N A Kogan M I Vlasova |
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Institution: | (1) Leningrad Pharmaceutical-Chemistry Institute, Russia |
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Abstract: | Aromatic aldehydes react with amides of 1-methylindole-2-carboxylic acid under acid catalysis conditions to give 1-aryl-4-methyldihydropyrrolo3,4-b]indol-3-ones. The intermediate 1-methyl-2-CONHR-3( -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. Dihydropyrrolo3,4-b] indol-3-ones were reduced by LiAlH4 to the corresponding dihydropyrrolo3,4-b] indoles. A mechanism for the formation of dihydropyrrolo3,4-b] indoles is proposed.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1516–1523, November, 1976. |
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