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Paper | Regular issue | Vol 83, No. 4, 2011, pp.777-787
Published online, 2nd March, 2011
DOI: 10.3987/COM-10-12133
Synthesis of 3-Alkanesulfonyl-4(1H)-quinolinones from 3-Alkanesulfonyl-4-alkylsulfanylquinolines

Leszek Skrzypek,* Andrzej Maślankiewicz, and Kinga Suwińska

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

Abstract

3-Alkanesulfonyl-4-alkylsulfanylquinolines (4) were transformed to 3-alkanesulfonyl-4(1H)-quinolinones (5) and (6). 1H-Derivatives 5 were obtained by acidic hydrolysis of compounds 4. 1-Alkyl derivatives 6 were prepared in three ways: a) via 1-alkylquinolinium salts 7 followed by their acidic hydrolysis to 6; b) in one-pot reactions of compounds 4 with alkyl bromides under Phase Transfer Catalysis (PTC) conditions; or c) by alkylation of 1H-derivatives 5 with alkyl bromides under PTC conditions.