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Synthesis of N-Tosylates of 4-Methoxy-1,2,3,4-tetrahydrocarbazole and 2-(6-Methoxy-1-cycloalken-1-yl)anilines

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Abstract

The reaction of N-tosylates of 2-(1-cycloalken-1-yl)anilines and 2,3,9a,9-tetrahydro-1H-carbazole with methanol in the presence of CuBr2 proceeds with high regioselectivity leading to the corresponding tosylates of 2-(6-methoxy-1-cycloalken-1-yl)anilines and 4-methoxy-1,2,3,4-tetrahydrocarbazole. The latter as well as N-mesyl-1,2,3,4-tetrahydrocarbazole showed moderate cytotoxic activity with respect to HEK293 cell line.

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Authors and Affiliations

  1. Bashkir State University, Ufa, Russia

    I. А. Kirillova & М. M. Zalimova

  2. Institute of Biochemistry and Genetics, Ufa Scientific Center, Russian Academy of Sciences, Ufa, Russia

    R. V. Mulyukova & Yu. V. Vakhitova

  3. Institute of Organic Chemistry, Russian Academy of Sciences, pr. Oktyabrya 71, Ufa, 450054, Russia

    R. N. Khusnitdinov & R. R. Gataullin

Authors
  1. I. А. Kirillova
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  2. М. M. Zalimova
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  3. R. V. Mulyukova
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  4. Yu. V. Vakhitova
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  5. R. N. Khusnitdinov
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  6. R. R. Gataullin
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Correspondence to R. R. Gataullin.

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Original Russian Text © I.А. Kirillova, М.M. Zalimova, R.V. Mulyukova, Yu.V. Vakhitova, R.N. Khusnitdinov, R.R. Gataullin, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 3, pp. 390–396.

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Kirillova, I.А., Zalimova, М.M., Mulyukova, R.V. et al. Synthesis of N-Tosylates of 4-Methoxy-1,2,3,4-tetrahydrocarbazole and 2-(6-Methoxy-1-cycloalken-1-yl)anilines. Russ J Gen Chem 88, 418–424 (2018). https://doi.org/10.1134/S1070363218030076

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