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Chemistry of Heterocyclic Compounds

, Volume 50, Issue 10, pp 1471–1477 | Cite as

Synthesis of 10,10-Dioxo-10λ6-Phenoxathiin Derivatives by Reaction of 4,4'-Oxydibenzoic Acid with Sulfur-Containing Electrophiles*

  • V. S. Yashchenko
  • A. A. Pap
  • G. V. Kalechits
  • A. V. Makey
  • V. K. Ol’khovik
Article

A method for the synthesis of 4-substituted derivatives of 10,10-dioxo-10λ6-phenoxathiin-2,8-dicarboxylic acid by the reaction of 4,4'-oxydibenzoic acid with strong sulfur-containing electrophiles was developed. The interaction with chlorosulfonic acid or oleum was shown to produce a phenoxathiin ring by initial substitution of hydrogen at positions 2 and 2' followed by intramolecular cyclization to 4-chlorosulfonyl(sulfo)-10,10-dioxo-10λ6-phenoxathiin-2,8-dicarboxylic acid. Using an analogous approach, methods for the synthesis of 4-nitro- and 4,6-dinitro-10,10-dioxo-10λ6-phenoxathiin-2,8-di-carboxylic acids were developed.

Keywords

aromatic dicarboxylic acids 4,4'-oxydibenzoic acid phenoxathiin polycyclic compounds cyclization electrophilic substitution 

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Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • V. S. Yashchenko
    • 1
  • A. A. Pap
    • 1
  • G. V. Kalechits
    • 1
  • A. V. Makey
    • 1
  • V. K. Ol’khovik
    • 1
  1. 1.Institute of Chemistry of New MaterialsNational Academy of Sciences of BelarusMinskBelarus

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