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Note | Regular issue | Vol 60, No. 6, 2003, pp.1387-1400
Published online, 31st March, 2003
DOI: 10.3987/COM-03-9732
Nitrothioquinanthrenes and Their S-Oxides

Maria J. Maslankiewicz* and Tadeusz Glowiak

*Institute of Chemistry, University of Silesia, Szkolna 9, 40-006 Katowice, Poland

Abstract

The reaction of dithiinodiquinolines (1) or (5) with an excess of nitrating mixture at 0-5 °C led within 3 days to the mixtures of nitrothioquinanthrene S-oxides (3a-d) or nitroisothioquinanthrene S-oxides (7a, b). Sulfoxides (3a-d) were reduced to sulfides (4a, b) with KI / aq. HCl system. Sulfides (4a, b) were reoxidised to sulfoxides (3a-d) with nitrating mixture. Structure of compounds (3a, 4a, b, 7b) was assigned by means of 1D and 2D 1H and 13C NMR spectral techniques. The structural conclusions were supported by an X-Ray analysis of 8-nitrothioquinanthrene 7-oxide (3a).