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Note | Regular issue | Vol 71, No. 1, 2007, pp.175-180
Published online, 1st December, 2006
DOI: 10.3987/COM-06-10922
Reactions of Some Dithiinodiquinoline 7-Oxides with Potassium Phenoxide

Maria J. Maslankiewicz and Andrzej Maslankiewicz*

*Department of Organic Chemistry, The Medical University of Silesia, Jagiellonska 4, 41-200 Sosnowiec, Poland

Abstract

S-Oxides of dithiinodiquinolines (4) and (5) react with potassium phenoxide at γ-quinolinyl-sulfur bond in two manners. Sulfinyl moiety at non-aza-influenced position in sulfoxide (5) significantly activates ortho-sulfanyl substituent towards nucleophilic phenoxy-de-sulfidation to form quinolinethiolate (6A). In the case of sulfoxide (4) with sulfinyl group in aza-activated position, nucleophilic phenoxy-de-sulfinylation occurs to form quinolinesulfenate anion (7A) trapped finally by methylation to products (8), (9) and (10).