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2005
Quinoline derivatives
R 0410
Azinyl Sulfides. Part 82. Synthesis of 1-Methyl-3-methylthio- and 1-Methyl2(1H)-Quinolinones. — The conversion of quinoli08- 150 -3-methylsulfinyl-4-substituted
nyl sulfides (I) into title quinolinones (IV) and (VI) requires the transformation of the
azamethin moiety of (I) to the N-alkyllactam pattern in (IV). The key-step for this route
is the reaction of quinolinium salts (III) with sodium hydroxide. Although this reaction
is carried out in the presence of the labile, nucleophilic sensitive 4-substituent, salts (III)
react mainly with the hydroxyl anion to give 1,2 adducts, which are further oxidized to
quinolinones (IV). The minor 1,4 adducts are finally converted to 4-quinolinones (V).
However, 2-quinolinone (VIII) is effectively prepared by amination of (VIc). S-oxidation of the methylthio group in (IV) is achieved by using equimolar amounts of nitric
acid, whereas an excess of nitric acid causes S-oxidation and nitration, cf. (IX). —
(CHROBAK, E.; MASLANKIEWICZ*, A.; Heterocycles 63 (2004) 10, 2329-2340;
Dep. Org. Chem., Silesian Sch. Med., PL-41-200 Sosnowiec, Pol.; Eng.) —
H. Hoennerscheid
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