4.7 Article

Iodine-Mediated Synthesis of 2-(Methylthio)-4H-chromen-4-ones and Study of Their Halogenation Reactions

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JOURNAL OF ORGANIC CHEMISTRY
卷 86, 期 14, 页码 9478-9489

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AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c00788

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  1. Department of Biotechnology (DBT), Ministry of Science and Technology, India
  2. The World Academy of Science (TWAS)
  3. University of Delhi
  4. ICMR
  5. CSIR

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An efficient iodine-mediated method has been developed for the synthesis of functionalized 2-(methylthio)-4H-chromen-4-ones, which serve as key precursors for various chemical reactions. Mechanistically, the intramolecular cyclization of ketene dithioacetal was observed to proceed through a radical pathway. 3-Halo-2-(methylthio)-4H-chromen-4-ones were obtained via various two- or one-pot halogenation approaches.
An efficient iodine-mediated method is developed for the synthesis of functionalized 2-(methylthio)-4H-chromen-4-ones by intramolecular cyclization of easily accessible 1-(2-benzyloxy-aryl)-3,3-bis-methylsulfanyl-propenones. The synthesized chromen-4-ones turn out to be a key precursor for various kinds of chemical reactions. Mechanistically, we observed that iodine-mediated intramolecular cyclization of ketene dithioacetal proceeded through a radical pathway. 3-Halo-2-(methylthio)-4H-chromen-4-ones were achieved via various two- or one-pot halogenation approaches.

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