Iminothiolactone-thiolactam rearrangement in the synthesis of 4-amino-6-thioxo-3,7,9-triazatricyclo-[6.2.1.01,5]undec-4-ene-2,10-diones

The reaction of 4-amino-8-hydroxy-1,6-dioxo-2,7-diazaspiro[4.4]non-3-ene-4-carbonitriles with Lawesson's reagent proceeded as an iminothiolactone-thiolactam rearrangement, leading to the formation of 4-amino-6-thioxo-3,7,9-triazatricyclo[6.2.1.01,5]undec-4-ene-2,10-diones.

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The study was performed within the framework of scholarship SP-2802.2015.4 awarded by the President of the Russian Federation to young scientists and graduate students.

The X-ray structural studies were performed by using equipment of the Chair of General Chemistry, Faculty of Chemistry, M. V. Lomonosov Moscow State University.

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Correspondence to Sergey V. Fedoseev.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(9), 1045–1049

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Fedoseev, S.V., Belikov, M.Y., Ershov, O.V. et al. Iminothiolactone-thiolactam rearrangement in the synthesis of 4-amino-6-thioxo-3,7,9-triazatricyclo-[6.2.1.01,5]undec-4-ene-2,10-diones. Chem Heterocycl Comp 53, 1045–1049 (2017). https://doi.org/10.1007/s10593-017-2167-9

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Keywords

  • iminothiolactone
  • Lawesson's reagent
  • spiroheterocycles
  • sulfur heterocycles
  • thiolactam
  • rearrangement