Synthesis and Transformations of Substituted 3,3′-Diquinolinyl Sulfides

Abstract

Reactions of the 1,4-dithiin ring opening in 1,4-dithiinodiquinoline 1 with selected oxygen nucleophiles followed by S- and N-alkylation led to sulfides possessing one or two quinolinyl or quinolonyl units. Diquinolinyl sulfides 2 were transformed into quinolinyl-quinolonyl sulfides 3 or diquinolonyl sulfides 9 via thermal rearrangement (the O-N alkyl migration) or hydrolysis of the alkoxy and alkylthio groups with the hydrochloric acid-ethanol mixture.

Keywords:

• 1,4-dithiinodiquinoline
• 4(1H)-quinolones
• diquinolyl sulfides
• ring opening

LXXXIII in the series of Azinyl Sulfides.