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Interaction of anilines substituted in ortho-positions by alkenyl groups with thionyl chloride

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Abstract

Dimethyl sulfoxide is one of the most commonly applied organic solvents in many organic reactions. It is known that DMSO/SOCl2 is the efficient system for the intramolecular cyclization of 2-alkenylanilines. The interaction of N-tosyl derivatives of 2-(cyclo)(alken-2-yl)- and 2-(cyclo)(alken-1-yl)anilines with thionyl chloride was studied in the DMSO/SOCl2 system. It was established that the structure of the obtained products depends on the structure of the alkenyl fragment and the reaction conditions. As a result of these reactions, methylsulfanyl(cyclo)alkyl products, indole, carbazole, or oxazepine were formed. The structure of new compounds was confirmed by IR, heteronuclear NMR spectroscopy, and high resolution mass spectrometry.

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Acknowledgements

This work was supported by the Ministry of Science and Higher Education of the Russian Federation as part of the state task no. 122031400278-2.

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Authors and Affiliations

  1. Laboratory of Organic Functional Materials, Ufa Institute of Chemistry of the Russian Academy of Sciences, Ufa, Russia

    Lyaysan R. Latypova, Gulsum S. Usmanova, Shamil M. Salikhov & Akhat G. Mustafin

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  1. Lyaysan R. Latypova
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  2. Gulsum S. Usmanova
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  3. Shamil M. Salikhov
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  4. Akhat G. Mustafin
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Correspondence to Lyaysan R. Latypova.

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Latypova, L.R., Usmanova, G.S., Salikhov, S.M. et al. Interaction of anilines substituted in ortho-positions by alkenyl groups with thionyl chloride. Monatsh Chem 154, 1275–1283 (2023). https://doi.org/10.1007/s00706-023-03122-y

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  • DOI: https://doi.org/10.1007/s00706-023-03122-y

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