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11.17.4.3.7.11 Variation 11: Replacement of Sulfur or Oxygen Groups by Carbon-Containing Substituents

DOI: 10.1055/sos-SD-011-00783

Kikelj, D.; Urleb, U.Science of Synthesis, (200211781.

Alkylsulfanyl derivatives can be prepared from corresponding thioxo derivatives.[‌761‌] The sulfur-bearing group of these compounds, as well as that of alkylsulfonylthiazoles,[‌1097‌] can be replaced by carbon nucleophiles. For example, 2-(methylsulfanyl)thiazoles can be used for the synthesis of C-functionalized as well as for the synthesis of N- and O-functionalized thiazoles.[‌1097‌,‌1098‌] The exchange of 2-alkylsulfanyl substituents in thiazolium salts 510 by C-nucleophiles, such as 2,6-dimethylquinoline 511 to afford the iodide 512,[‌761‌] is used in the synthesis of methincyan dyes (Scheme 218).

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