AI Article Synopsis

  • - A new method for creating furocoumarins was established using a reaction between oxime esters and 4-hydroxycoumarins, mediated by iodine as a radical initiator.
  • - The mechanism revealed that an α-iodoimine intermediate plays a crucial role in successfully completing the ring-closing step of the reaction.
  • - This approach showed good versatility with various functional groups and has the potential for broader applications in synthesizing other heterocyclic compounds.

Article Abstract

A novel synthesis of furocoumarins was developed by a reaction between oxime esters and 4-hydroxycoumarins. The reaction was proposed to undergo radical mechanism mediated by iodine, a cheap and common laboratory reagent. Mechanistic studies showed the key for the successful transformation was the presence of α-iodoimine intermediate which facilitated the ring-closing step. The developed conditions produced good functional group tolerance with a wide range of high-profile furocoumarin product. The potential for this strategy to be applied in other syntheses of heterocyclic compounds is highly achievable.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9058646PMC
http://dx.doi.org/10.1039/d0ra07566cDOI Listing

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