Issue 72, 2020

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
03 Sept. 2020
Accepted
27 Nov. 2020
First published
16 Dec. 2020
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2020,10, 44332-44338

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

Q. T. Pham, P. Q. Le, H. V. Dang, H. Q. Ha, H. T. D. Nguyen, T. Truong and T. M. Le, RSC Adv., 2020, 10, 44332 DOI: 10.1039/D0RA07566C

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