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Iodine-mediated formal [3 + 2] annulation for synthesis of furocoumarin from oxime esters.

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.

SUBMITTER: Pham QT

PROVIDER: S-EPMC9058646 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature

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Iodine-mediated formal [3 + 2] annulation for synthesis of furocoumarin from oxime esters.

Pham Quyen T QT Le Phong Q PQ Dang Ha V HV Ha Hiep Q HQ Nguyen Huong T D HTD Truong Thanh T Le Tri Minh TM

RSC advances 20201216 72

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. T ...[more]

PMID: 35517165

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