Reaction of 3',4-di(alkylthio)-3,4'-diquinolinyl sulfides 1 with nitrating
mixture started with 3'-methylthio group monooxidation and yielded the 3'-a
lkylsulfinyl diquinolinyl sulfides 2 as the primary products. Further treat
ment of 2 with nitrating mixture proceeded as 4-alkylthio group oxidation t
o give the mixture of disulfoxides 3 and 4, which underwent hydrolysis (in
90% sulfuric acid) to 3'-alkylsulfinyl-4(1H)-quinolinones 5.