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Paper | Regular issue | Vol 75, No. 11, 2008, pp.2649-2657
Published online, 16th June, 2008
DOI: 10.3987/COM-08-11421
1-Alkyl-3-ethylthio-4-(N-benzoyl-N-phenylamino)quinolinium Salts — Synthesis and Transformations

Andrzej Zieba* and Kinga Suwinska

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

Abstract

The reaction of 1-alkyl-4-(phenylamino)quinolinium 3-thiolates (2) with benzoyl chloride leads to 1-alkyl-3-benzoylthio-4-(phenylamino)quinolinium chloride (6). In the presence of DABCO, compounds (6) split off hydrogen chloride yielding 1-alkyl-3-benzoylthio-1,4-dihydro-4-(phenylimino)quinoline (7). Alkyla-tion of 4-(phenylimino)quinoline (7) with ethyl bromide leads to 1-alkyl-3-ethylthio-4-(N-benzoyl-N-phenylamino)quinolinium bromide (10). The structure of the obtained compounds were analyzed using 1H NMR (NOE) and 15N NMR spectral methods. The structure of compound (10a) was confirmed by X-ray analysis.