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A novel regiospecific cascade synthesis of sulfonamide derivatives from N-(2-polychloroethyl)sulfonamides via chloroaziridine intermediates in the presence of mercaptoethanol

  • SI - MCR2009
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Abstract

N-(1-Aryl-2-polychloroethyl)arenesulfonamides obtained on the basis of N,N-dichlorosulfoamides and polychloroethenes or phenylacetylene undergo a reaction cascade in the presence of mercaptoethanol. The reaction cascade opens a new route to the series of cyclic or open-chain sulfonamide derivatives. The process includes cyclization to aziridine intermediates, their further recyclization, and isomerization to imidoylchlorides or chloroimines, followed by substitution or reduction under the action of mercaptoethanol or hydrolysis. The final sulfonamide structures depend on the starting N-(polychloroethyl)sulfonamides. N-(2,2-Dichloroethyl)sulfonamides were transformed into sulfonamide-containing 1,4-oxathians while N-(2,2,2-trichloroethyl)sulfonamides were converted to N-(2-arylacetyl)arenesulfonamides. N-(2-Phenyl-2,2-dichloroethyl)sulfonamides form enamide derivatives that were transformed into aromatic ketones.

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Authors and Affiliations

  1. A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of Russian Academy of Sciences, 1 Favorsky Str., 664033, Irkutsk, Russia

    Igor B. Rozentsveig, Aleksandr V. Popov, Gulnur N. Rozentsveig, Valeriy Yu. Serykh, Kirill A. Chernyshev, Leonid B. Krivdin & Galina G. Levkovskaya

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  1. Igor B. Rozentsveig
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  2. Aleksandr V. Popov
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  3. Gulnur N. Rozentsveig
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  4. Valeriy Yu. Serykh
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  5. Kirill A. Chernyshev
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  6. Leonid B. Krivdin
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  7. Galina G. Levkovskaya
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Correspondence to Igor B. Rozentsveig.

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4th International Conference on Multi-Component Reactions and Related Chemistry, Russia, Ekaterinburg, 2009.

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Rozentsveig, I.B., Popov, A.V., Rozentsveig, G.N. et al. A novel regiospecific cascade synthesis of sulfonamide derivatives from N-(2-polychloroethyl)sulfonamides via chloroaziridine intermediates in the presence of mercaptoethanol. Mol Divers 14, 533–541 (2010). https://doi.org/10.1007/s11030-010-9231-z

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