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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Iodine-mediated formal [3 + 2] annulation for synthesis of furocoumarin from oxime esters
Quyen T Pham1, Phong Q Le2, Ha V Dang1
1School of Medicine, VNU-HCM Linh Trung Ward, Thu Duc District Ho Chi Minh City Vietnam leminhtri@ump.edu.vn.
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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