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

✍ Scribed by Andrzej Maślankiewicz; Stanistaw Boryczka

• Publisher: Elsevier Science
• Year: 2010
• Tongue: English
• Weight: 638 KB
• Volume: 112
• Category: Article
• ISSN: 0165-0513
• DOI: 10.1002/recl.19931121002

✦ Synopsis

Abstract

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 (18.5–91.5%) and, in some cases, 1,4‐dihydro‐4‐oxo‐3′‐(alkylthio)‐3,4′‐diquinolinyl sulfides 4a (up to 31.5%). 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.