Chemistry of Heterocyclic Compounds

, Volume 24, Issue 9, pp 1046–1050 | Cite as

Condensed thiolane 1,1-dioxide systems. 2. Brominated cis-perhydrothieno[3,4-d]oxazoles and imidazoles

  • V. I. Slutskii
  • L. N. Shevchenko


Bromocyclization of 2-bromo-4-ureido-2-thiolene 1,1-dioxide has given perhydrothieno[3,4-d]oxazol-2-imino 5,5-dioxide, in which hydrogen atoms are absent from one of the α-methylene groups. In weakly basic media, this undergoes conversion into the corresponding aminooxazoline. Treatment of an aqueous solution of 2-bromo-4-ureido-2-thiolene 1,1-dioxide with bases gives a mixture of perhydrothieno[3,4-d]imidazol-2-one 5,5-dioxides in which the bromine atoms have the exo- and endo-orientations. In all the bicyclic compounds, the two rings are cis-fused.


Hydrogen Aqueous Solution Organic Chemistry Hydrogen Atom Thiolane 
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Copyright information

© Plenum Publishing Corporation 1989

Authors and Affiliations

  • V. I. Slutskii
    • 1
  • L. N. Shevchenko
    • 1
  1. 1.Department of Petroleum ChemistryInstitute of Physical Organic and Carbon Chemistry of the Ukrainian SSRKiev

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