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Heterocyclic Thiones and Their Analogs in Reactions of 1,3-Dipolar Cycloaddition: III. Reaction of Benzothiazole-2-thione with a Double Excess of Nitrilimine

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Abstract

Main products of reaction between benzothiazole-2-thione and a double excess of nitrilimine are substituted 1-aryl-1-(1,3-benzothiazol-2-yl)-2-(2,3-dihydro-1,3,4-thiadiazol-2-yl)hydrazines. In the first step presumably forms a spiro compound via 1,3-dipolar cycloaddition of nitrilimine molecule to the C=S bond of the benzothiazolethione. The second nitrilimine molecule adds to the new C=S bond of the intermediate product arising by the rupture of CS bond in the thiadiazole ring of the spiro compound.

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REFERENCE

  1. Firsova, O.V., Dolgushina, T.S., Polukeev, V.A., Zavodnik, V.E., Stash, A.I., Bel'skii, V.K., and Galishev, V.A., Zh. Org. Khim., 2004, vol. 40, p. 1059.

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Authors and Affiliations

  1. St. Petersburg State Technological Institute, St. Petersburg, 198013, Russia

    O. V. Firsova, T. S. Dolgushina & V.A. Galishev

  2. Closed Joint-stock Company “Vekton”, St. Petersburg

    B. A. Polukeev & V. E. Zavodnik

  3. State Scientific Center of Russian FederationKarpov Physicochemical Research Institute, Moscow, Russia

    A. I. Stash & V. K. Bel'skii

Authors
  1. O. V. Firsova
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  2. T. S. Dolgushina
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  3. B. A. Polukeev
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  4. V. E. Zavodnik
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  5. A. I. Stash
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  6. V. K. Bel'skii
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  7. V.A. Galishev
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Firsova, O.V., Dolgushina, T.S., Polukeev, B.A. et al. Heterocyclic Thiones and Their Analogs in Reactions of 1,3-Dipolar Cycloaddition: III. Reaction of Benzothiazole-2-thione with a Double Excess of Nitrilimine. Russian Journal of Organic Chemistry 40, 1175–1180 (2004). https://doi.org/10.1023/B:RUJO.0000045901.75965.de

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  • DOI: https://doi.org/10.1023/B:RUJO.0000045901.75965.de

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