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Copper-Catalyzed One-Pot Synthesis of 2‑Arylthiochromenones: An in Situ Recycle of Waste Byproduct as Useful Reagent

Copper-catalyzed one-pot synthesis of various 2-arylthiochromenones is developed using xanthate as an odorless sulfur source from easily acquirable 2′-halochalcones. This methodology demonstrates that the cross-coupled product thiochromanone synthesized from 2′-halochalcones (upstream reaction) is o...

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Bibliographic Details
Published in:Organic letters 2019-01, Vol.21 (1), p.75-79
Main Authors: Sangeetha, Subramani, Sekar, Govindasamy
Format: Article
Language:English
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Summary:Copper-catalyzed one-pot synthesis of various 2-arylthiochromenones is developed using xanthate as an odorless sulfur source from easily acquirable 2′-halochalcones. This methodology demonstrates that the cross-coupled product thiochromanone synthesized from 2′-halochalcones (upstream reaction) is oxidized to thiochromenone (downstream reaction) in the same pot using waste byproduct (KI) of the first step as powerful oxidant molecular iodine (I2). This one-pot synthesis has been further extended for the synthesis of 3,3′-methylenebisthioflavone using dimethyl sulfoxide (DMSO) as solvent and methylene source.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b03508