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1,3-Dipolar cycloaddition of 3-phenylamino-5-phenylimino-1,2,4-dithiazole to 1-acyl-2-phenylacetylenes—A new route to functionalized 1,3-thiazole derivatives

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Abstract

3-Phenylamino-5-phenylimino-1,2,4-dithiazole reacted with 1-acyl-2-phenylacetylenes in ethanol or toluene on heating (78–80°C, 1 h) in chemo- and regioselective fashion to give previously unknown N-[5-acyl-3,4-diphenyl-1,3-thiazol-2(3H)-ylidene]-N′-phenylthioureas (yield 57–60%). The structure of N-[5-benzoyl-3,4-diphenyl-1,3-thiazol-2(3H)-ylidene]-N′-phenylthiourea was proved by X-ray analysis.

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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

    T. E. Glotova, M. Yu. Dvorko & A. I. Albanov

  2. Institute of Chemical Physics Problems, Russian Academy of Sciences, Chernogolovka, Moscow oblast, Russia

    O. N. Kazheva, G. V. Shilov & O. A. D’yachenko

Authors
  1. T. E. Glotova
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  2. M. Yu. Dvorko
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  3. A. I. Albanov
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  4. O. N. Kazheva
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  5. G. V. Shilov
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  6. O. A. D’yachenko
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Correspondence to T. E. Glotova.

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Dedicated to Full Member of the Russian Academy of Sciences B.A. Trofimov on his 70th anniversary

Original Russian Text © T.E. Glotova, M.Yu. Dvorko, A.I. Albanov, O.N. Kazheva, G.V. Shilov, O.A. D’yachenko, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 10, pp. 1554–1558.

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Glotova, T.E., Dvorko, M.Y., Albanov, A.I. et al. 1,3-Dipolar cycloaddition of 3-phenylamino-5-phenylimino-1,2,4-dithiazole to 1-acyl-2-phenylacetylenes—A new route to functionalized 1,3-thiazole derivatives. Russ J Org Chem 44, 1532–1537 (2008). https://doi.org/10.1134/S1070428008100230

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  • DOI: https://doi.org/10.1134/S1070428008100230

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