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Paper | Regular issue | Vol 60, No. 9, 2003, pp.2065-2076
Published online, 18th August, 2003
DOI: 10.3987/COM-03-9816
1H- and 1-Alkyl-1,4-dihydro-4-oxo-3-alkylthioquinolines from 1,4-Dihydro-4-oxo-3’-alkylthio-3,4’-diquinolinyl Sulfides

Ewa Bebenek, Elwira Chrobak, and Andrzej Maslankiewicz*

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

Abstract

Quinolinones (1) were N-alkylated with alkyl iodides in DMSO or DMF in the presence of potassium methoxide to N-alkyl derivatives (3) (78-98%). One-pot method was elaborated allowing to transform compound (1a) into the mixture of 1-alkyl-3-alkylthio-4(1H)-quinolinones (8) (55-76%) and 4-methoxy-3-methylthioquinoline (4a) (83-90 %).
Potassium methoxide in DMSO causes sequentially fission of diquinolinyl sulfide (1) to the mixture of dipotassium salt of 3-mercapto-4-quinolinone (9) and (4) and then O-demethylation of 4 to potassium salt of 3-alkylthio-4-quinolinone (5), which could be transformed after S-alkylation of 9 and neutralization to 3-alkylthio-4-quinolinones (6). This one-pot procedure permits to convert both quinoline-units of 3,4’-diquinolinyl sulfide (1) to 6 with total yield of 60-78%.