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Cascade synthesis of 2-amino-5-(4-methoxyphenyl)-4-phenyl-1,3-thiazole by reaction of 4-chloro-N-[2,2-dichloro-1-(4-methoxyphenyl)-2-phenylethyl]benzenesulfonamide with thiourea

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Abstract

4-Chloro-N-[2,2-dichloro-1-(4-methoxyphenyl)-2-phenylethyl]benzenesulfonamide reacted with thiourea on heating in DMF in the presence of sodium carbonate to give 5-(4-methoxyphenyl)-4-phenyl-1,3-thiazole-2-amine. A probable reaction scheme includes cyclization of the initial N-dichloroethyl amide to N-sulfonyl-2,3-diaryl-2-chloroaziridine which undergoes isomerization with opening of the three-membered ring to 1-arylsulfonylamino-2-chloro-2-(4-methoxyphenyl)-1-phenylethene. The subsequent heterocyclization in the reaction with thiourea is accompanied by aromatization via elimination of the arenesulfonamide fragment.

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Authors and Affiliations

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

    G. N. Rozentsveig, V. Yu. Serykh, K. A. Chernyshev, I. B. Rozentsveig, G. G. Levkovskaya & L. B. Krivdin

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  1. G. N. Rozentsveig
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  2. V. Yu. Serykh
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  3. K. A. Chernyshev
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  4. I. B. Rozentsveig
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  5. G. G. Levkovskaya
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  6. L. B. Krivdin
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Correspondence to G. N. Rozentsveig.

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Original Russian Text © G.N. Rozentsveig, V.Yu. Serykh, K.A. Chernyshev, I.B. Rozentsveig, G.G. Levkovskaya, L.B. Krivdin, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 4, pp. 569–573.

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Rozentsveig, G.N., Serykh, V.Y., Chernyshev, K.A. et al. Cascade synthesis of 2-amino-5-(4-methoxyphenyl)-4-phenyl-1,3-thiazole by reaction of 4-chloro-N-[2,2-dichloro-1-(4-methoxyphenyl)-2-phenylethyl]benzenesulfonamide with thiourea. Russ J Org Chem 47, 572–576 (2011). https://doi.org/10.1134/S1070428011040178

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  • DOI: https://doi.org/10.1134/S1070428011040178

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