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

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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References

  1. D. Gavriliu, S. Stoia, S. Florea, and O. Maior, An. Univ. Bucuresti, Chim, 6, 105 (1997).

    CAS  Google Scholar 

  2. A. A. Aly and A. A. F. Wasfy, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 43B, 629 (2004).

    CAS  Google Scholar 

  3. A. A. Aly and A. A. F. Wasfy, Chem. Pap., 58, 126 (2004).

    CAS  Google Scholar 

  4. C. T. Supuran, A. Scozzafava, F. Briganti, G. Loloiu, and O. Maior, Eur. J. Med Chem., 33, 821 (1998).

    Article  CAS  Google Scholar 

  5. M. S. Behalo, J. Sulfur Chem., 31, 287 (2010).

    Article  CAS  Google Scholar 

  6. M. Harfenist, D. P. C. McGee, M. D. Reeves, and H. L. White, J. Med. Chem., 41, 2118 (1998).

    Article  CAS  Google Scholar 

  7. M. Ueda, T. Aizawa, and Y. Imai, J. Polym. Sci., Polym. Chem. Ed., 15, 2739 (1977).

    Article  CAS  Google Scholar 

  8. K. Niume, K. Nakamichi, F. Toda, K. Uno, M. Hasegawa, and Y. Iwakura, J. Polym. Sci., Polym. Chem. Ed., 18, 2163 (1980).

    Article  CAS  Google Scholar 

  9. T. Ashok Reddy and M. Srinivasan, J. Polym. Sci., Part A: Polym. Chem., 25, 2327 (1987).

    Article  Google Scholar 

  10. S. Ionescu, D. Gavriliu, O. Maior, and M. Hillebrand, J. Photochem. Photobiol., A, 124, 67 (1999).

  11. S. Ionescu, D. Popovici, A. T. Balaban, and M. Hillebrand, Spectrochim. Acta, Part A, 66, 1165 (2007).

    Article  Google Scholar 

  12. S. L. Razina, A. M. Gritsev, V. K. Ol'khovik, G. V. Kalechits, and N. V. Yukhimets, BY Pat. 8072; Af. Byul. Resp. Belarus No. 3, 83 (2006).

  13. V. K. Ol'khovik and G. V. Kalechits, Vesci NAN Belarusi, Ser. Khim. Navuk, No. 4, 75 (2013).

  14. S. Gaurhier and J. M. J. Frechet, Synthesis, 383 (1987).

  15. A. S. Guram, R. A. Rennels, and S. L. Buchwald, Angew. Chem., Int. Ed. Engl., 34, 1348 (1995).

    Article  CAS  Google Scholar 

  16. I. P. Beletskaya and A. V. Cheprakov, Organometallics, 31, 7753 (2012).

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Institute of Chemistry of New Materials, National Academy of Sciences of Belarus, 36 Fr. Skarina St., Minsk, BY-220141, Belarus

    V. S. Yashchenko, A. A. Pap, G. V. Kalechits, A. V. Makey & V. K. Ol’khovik

Authors
  1. V. S. Yashchenko
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  2. A. A. Pap
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  3. G. V. Kalechits
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  4. A. V. Makey
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  5. V. K. Ol’khovik
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Corresponding author

Correspondence to V. K. Ol’khovik.

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*Dedicated to Professor Gunars Duburs on the occasion of his 80th birthday.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1596–1603, October, 2014.

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Yashchenko, V.S., Pap, A.A., Kalechits, G.V. et al. Synthesis of 10,10-Dioxo-10λ6-Phenoxathiin Derivatives by Reaction of 4,4'-Oxydibenzoic Acid with Sulfur-Containing Electrophiles*. Chem Heterocycl Comp 50, 1471–1477 (2015). https://doi.org/10.1007/s10593-014-1612-2

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  • DOI: https://doi.org/10.1007/s10593-014-1612-2

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