Copper catalyzed one-pot synthesis of 2-arylthiochromenones has been developed from 2’-iodochalcones via 2-arylthiochromanones using xanthate as sulfur surrogate. A diversity of thiochromenones has been synthesized from 2’-iodochalcones or 2’-bromochalcones in good to excellent yield. This methodology utilizes the in situ reagent of iodine from iodide leaving group which is oxidized by dimethyl sulfoxide using sulphuric acid. The mechanism proceeds through α-iodination followed by dehydroiodination of in situ prepared 2-arylthiochromanones from 2'-iodo/bromochalcones. Furthermore, the methodology has been successfully extended for flavanones leading to flavones.

Novel Cu-catalyzed one-pot synthesis of 2-arylthiochromenones: Advantages of leaving group as an in-situ reagent

255th National Meeting (2018)

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