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Transition metal-catalyzed C,C- and C,N-cycloaminomethylation reactions of pyrrole and indole

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Chemistry of Heterocyclic Compounds Aims and scope

Catalytic cycloaminomethylation of pyrrole with bis(methoxymethyl)alkylamines or a mixture of alkyl(phenyl)amines and paraformaldehyde in the presence of [Ni(Py)4Cl2]·0.76H2O or NiCl2·6H2O catalysts proceeded at positions 2 and 5 of pyrrole ring. Cycloaminomethylation of indole was accomplished effectively at positions 1 and 3 in the presence of ZrOCl2·8H2O catalyst. When carbazole was treated with bis(methoxymethyl)alkylamine in the presence of ZrOCl2·8H2O catalyst, it was converted to N-aminomethylated product – N-[(9H-carbazol-9-yl)methyl]-N-(methoxymethyl)alkylamine.

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This work was performed with financial support from the Russian Foundation for Basic Research and the Academy of Sciences of the Bashkortostan Republic (project No. 17-43-020292 r_a) and the project part of the

State Assignment АААА-А117 012610060-7 (2017–2019). Structural characterization of the obtained compounds was performed on the equipment at the Regional Collective Use Center “Agidel”.

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Authors and Affiliations

  1. Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, 141 Oktyabrya Ave., Ufa, 450075, Russia

    Vnira R. Akhmetova, El’mira M. Bikbulatova, Nail S. Akhmadiev & Askhat G. Ibragimov

  2. Institute of Biology, Ufa Science Center, Russian Academy of Sciences, 69 Oktyabrya Ave., Ufa, 450054, Russia

    Nailya F. Galimzyanova

  3. Ufa State Petroleum Technological University, 1 Kosmonavtov St., Ufa, 450062, Russia

    Raikhana V. Kunakova

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  1. Vnira R. Akhmetova
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  2. El’mira M. Bikbulatova
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  3. Nail S. Akhmadiev
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  4. Nailya F. Galimzyanova
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  5. Raikhana V. Kunakova
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  6. Askhat G. Ibragimov
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Correspondence to Vnira R. Akhmetova.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(5), 520–527

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Akhmetova, V.R., Bikbulatova, E.M., Akhmadiev, N.S. et al. Transition metal-catalyzed C,C- and C,N-cycloaminomethylation reactions of pyrrole and indole. Chem Heterocycl Comp 54, 520–527 (2018). https://doi.org/10.1007/s10593-018-2299-6

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  • DOI: https://doi.org/10.1007/s10593-018-2299-6

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