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Paper | Regular issue | Vol 63, No. 10, 2004, pp.2329-2340
Published online, 23rd August, 2004
DOI: 10.3987/COM-04-10181
Synthesis of 1-Methyl-3-methylthio- and 1-Methyl-3-methylsulfinyl-4-substituted 2-(1H)-Quinolinones

Elwira Chrobak and Andrzej Maslankiewicz*

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

Abstract

Treatment of 4-substituted (X=Cl, OCH3, SCH3) quinolinium salts (2) in aqueous-DMSO solution with K3[Fe(CN)6] / NaOH system led to the respective 2-quinolinones (3) (60-69 %) which were accompanied by 1-methyl-
3-methylthio-4-quinolinone (8) (ca. 20%). 3-Methylthio substituent in quinolines (1), 4-quinolinethione (5) and 2-quinolinones (3) underwent S-oxidation to a sulfinyl group when the compounds (1), (3) and (5) were treated with nitrating mixture (-5 °C, 1 mol. eqv. of HNO3), but with an excess of nitric acid 2-quinolinones (3) were transformed to the respective 3-methylsulfinyl-6-nitro derivatives (7). The reaction of 4-chloroquinolines (1a), (3a) (at 140-160 °C) and (4a) (at 0 °C) with dimethylamine gave high yield of the 4-dimethylamino derivatives (1d), (3d) and (4d), respectively.