4-Alkoxy-3'-(alkylthio)-3,4'-diquinolinyl sulfides and 4-alkoxy-3-(alkylthio)quinolines

Article abstract of DOI:10.1002/recl.19931121002

The reactions of thioquinanthrene (1) with sodium alkoxides derived from 23 alcohols followed by S-alkylation gave the title 4-alkoxy-3'-(alkylthio)-3,4'-diquinolinyl sulfides 3 (18.5-91.5percent) and, in some cases, 1,4-dihydro-4-oxo-3'-(alkylthio)-3,4'-diquinolinyl sulfides 4a (up to 31.5percent).The effect of the solvent applied, counter-cation used and type of the alkyl group of alkoxide ions was then studied by means of competitive reactions.Effective transformation of 4-alkoxy-3'-(alkylthio)-3,4'-diquinolinyl sulfides 3 into some 4-alkoxy- and 4-(alkylthio)-3-(alkylthio)quinolines (5,6) and a one-pot preparation of 4-alkoxy-3-(alkylthio)quinolines 5 starting from thioquinanthrene (1) and sodium alkoxides were also presented.