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Synthesis of new thioxanthenes by organocatalytic intramolecular Friedel–Crafts reaction

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journal contribution
posted on 2018-07-16, 15:05 authored by Tülay Yildiz

An efficient organocatalytic route has been developed to synthesize novel substituted thioxanthenes (2a2v) starting from diaryl thioether alcohols (1a1v) using the intramolecular Friedel–Crafts reaction. The starting materials were obtained in two stages via a coupling reaction followed by the Grignard reaction. In this study, we tried for the first time to use some organic Brønsted acids as organocatalysts (3a3h) in the intramolecular Friedel–Crafts cyclization reaction of thioether alcohols. The synthesis of original substituted thioxanthenes was achieved within 15 minutes by using N-triflylphosphoramide (3h) with quantitative yields in THF at room temperature.

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