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Chemistry of Heterocyclic Compounds

, Volume 53, Issue 9, pp 1045–1049 | Cite as

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

  • Sergey V. FedoseevEmail author
  • Mikhail Yu. Belikov
  • Oleg V. Ershov
  • Victor A. Tafeenko
Article
  • 51 Downloads

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.

Keywords

iminothiolactone Lawesson's reagent spiroheterocycles sulfur heterocycles thiolactam rearrangement 

Notes

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.

Supplementary material

10593_2017_2167_MOESM1_ESM.pdf (1.1 mb)
ESM 1 (PDF 1089 kb)

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2017

Authors and Affiliations

  • Sergey V. Fedoseev
    • 1
    Email author
  • Mikhail Yu. Belikov
    • 1
  • Oleg V. Ershov
    • 1
  • Victor A. Tafeenko
    • 2
  1. 1.Chuvash State University named after I. N. UlyanovCheboksaryRussia
  2. 2.M. V. Lomonosov Moscow State UniversityMoscowRussia

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