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Paper | Regular issue | Vol 68, No. 3, 2006, pp.495-503
Published online, 21st February, 2006
DOI: 10.3987/COM-05-10654
1-Alkyl-4-(3-pyridinylamino)quinolinium-3-thiolates and Their Transformation into New Diazaphenothiazine Derivatives

Andrzej Zieba* and Kinga Suwinska

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

Abstract

The reactions of 5,12-dialkylthioquinantrenediinium bis-salts (1) with 3-aminopyridine yield 1-alkyl-4-(3-pyridinylamino)quinolinium-3-thiolates (2). In the presence of oxygen and hydrogen chloride, the compounds (2) undergo cyclization to 1,4-thiazine derivatives having the structure of 5-alkyl-12(H)-pyrido[2,3-e]quino[3,4-b][1,4]thiazinium salts (4). The structure of 3-thiolates (2) was analyzed using 1H NMR (NOE) and 15N NMR spectral methods. The structure of compound (4) was confirmed by X-Ray analysis.