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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
Article

Abstract

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.

Keywords

Hydrogen Aqueous Solution Organic Chemistry Hydrogen Atom Thiolane 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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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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