Open Access Open Access  Restricted Access Subscription Access

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

В. С. Ященко, А. А. Пап, Г. В. Калечиц, А. В. Макей, В. К. Ольховик
Cover Image

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


Keywords


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

Full Text: PDF (Russian) Supplementary File(s): None


 

 

Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv