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Aminomethylation of substituted pyrroles and 4,5,6,7-tetrahydroindoles with biogenic cyclic amines

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Abstract

Aminomethylation of 2-methyl(aryl)-, 2-aryl-3-alkylpyrroles, 4,5,6,7-tetrahydroindole and its 1-vinyl- and 1-benzyl-substituted derivatives with a mixture of 5% water-ethanol solution of formaldehyde and cyclic amine (pyrrolidine, piperazine, and morpholine) without catalyst at room temperature leads to the formation of the corresponding 2-aminomethylpyrroles and 2-aminomethyl-4,5,6,7-tetrahydroindoles in up to 92% yields. In reaction of 1-vinyl-4,5,6,7-tetrahydroindole with formaldehyde water solution and piperazine in a 60% yield 1,4-bis(1-vinyl-4,5,6,7-tetrahydroindol-2-yl)piperazine was obtained, a promising bifunctional monomer and a building block for the synthesis of new indole derivatives, in particular, of biologically active polymers. In the reaction of 2-methylpyrrole and 4,5,6,7-tetrahydroindole with formaldehyde and morpholine along with the С2-aminomethylation the 1-hydroxymethylation of the pyrrole ring was observed.

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Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    M. V. Markova, L. N. Sobenina, I. A. Ushakov, A. V. Ivanov & B. A. Trofimov

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  1. M. V. Markova
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  2. L. N. Sobenina
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  3. I. A. Ushakov
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  4. A. V. Ivanov
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  5. B. A. Trofimov
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Correspondence to B. A. Trofimov.

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Original Russian Text © M.V. Markova, L.N. Sobenina, I.A. Ushakov, A.V. Ivanov, B.A. Trofimov, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 2, pp. 196–202.

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Markova, M.V., Sobenina, L.N., Ushakov, I.A. et al. Aminomethylation of substituted pyrroles and 4,5,6,7-tetrahydroindoles with biogenic cyclic amines. Russ J Org Chem 53, 184–191 (2017). https://doi.org/10.1134/S1070428017020075

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