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

I. А. Kirillova; М. M. Zalimova; R. V. Mulyukova; Yu. V. Vakhitova; R. N. Khusnitdinov; R. R. Gataullin

doi:10.1134/S1070363218030076

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

Authors: Kirillova I.А.¹, Zalimova М.M.¹, Mulyukova R.V.², Vakhitova Y.V.², Khusnitdinov R.N.³, Gataullin R.R.³
Affiliations:
1. Bashkir State University
2. Institute of Biochemistry and Genetics, Ufa Scientific Center
3. Institute of Organic Chemistry
Issue: Vol 88, No 3 (2018)
Pages: 418-424
Section: Article
URL: https://journal-vniispk.ru/1070-3632/article/view/222046
DOI: https://doi.org/10.1134/S1070363218030076
ID: 222046

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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.