Desymmetrization Reactions of Indigo with Grignard Reagents for the Synthesis of Selective Antiplasmodial [1,3']-3-Aryl-2,2'-diindol-3'-ones.

Author(s) Butler, N.M.; Bremner, J.B.; Willis, A.C.; Lucantoni, L.; Avery, V.M.; Keller, P.A.
Journal J Org Chem
Date Published 2019 Sep 06

The nucleophilic addition of organomagnesium and organolithium species to the cheap and robust natural dye indigo led to desymmetrization of the heterocyclic nucleus via a Grignard addition-dehydration procedure. Twenty-seven diversely functionalized [1,3']-3-substituted 2,2'-diindol-3'-ones were synthesized by this methodology, with several showing submicromolar inhibition and exquisite selectivity against parasites (3D7 and Dd2 strains) . This work demonstrates the utility of indigo dye as a highly versatile scaffold for the synthesis of structurally diverse, bioactive heterocycles.

DOI 10.1021/acs.joc.9b01442
ISSN 1520-6904
Citation J Org Chem. 2019;84(17):1122811239.

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