SYNTHESIS OF 10,10-DIOXO-10λ6-PHENOXATHIIN DERIVATIVES BY REACTION OF 4,4'-OXYDIBENZOIC ACID WITH SULFUR-CONTAINING ELECTROPHILES

Authors

  • В. С. Ященко Institute of Chemistry of New Materials, National Academy of Sciences of Belarus
  • А. А. Пап Institute of Chemistry of New Materials, National Academy of Sciences of Belarus
  • Г. В. Калечиц Institute of Chemistry of New Materials, National Academy of Sciences of Belarus
  • А. В. Макей Institute of Chemistry of New Materials, National Academy of Sciences of Belarus
  • В. К. Ольховик Institute of Chemistry of New Materials, National Academy of Sciences of Belarus

DOI:

https://doi.org/10.1007/1900

Keywords:

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

Abstract

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.

How to Cite
Yashchenko, V. S.; Pap, A. A.; Kalechits, G. V.; Makey, A. V.; Ol'khovik, V. K. Chem. Heterocycl. Compd. 2015, 50, 1471. [Khim. Geterotsikl. Soedin. 2014, 1596.]

For this article in the English edition see DOI 10.1007/s10593-014-1612-2

Author Biographies

В. С. Ященко, Institute of Chemistry of New Materials, National Academy of Sciences of Belarus

Владимир Сергеевич Ященко

А. А. Пап, Institute of Chemistry of New Materials, National Academy of Sciences of Belarus

Андрей Анатольевич Пап

Г. В. Калечиц, Institute of Chemistry of New Materials, National Academy of Sciences of Belarus

Галина Викторовна Калечиц

А. В. Макей, Institute of Chemistry of New Materials, National Academy of Sciences of Belarus

Анна Валерьевна Макей

В. К. Ольховик, Institute of Chemistry of New Materials, National Academy of Sciences of Belarus

Вячеслав Константинович Ольховик

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Published

2014-10-15

Issue

No. 10 (2014)

Section

Original Papers