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Cascade reactions of indigo with oxiranes and aziridines: efficient access to dihydropyrazinodiindoles and spiro-oxazocinodiindoles

Butler, Nicholas M; Hendra, Rudi; Bremner, John B; Willis, Anthony; Lucantoni, Leonardo; Avery, Vicky M; Keller, Paul


The base-initiated alkylation of the abundant natural dye indigo 1 with ring-strained electrophiles results in the unprecedented, one-pot synthesis of functionalised dihydropyrazino[1,2-a:4,3-a]diindoles, dihydroepoxy[1,5]oxazocino[5,4-a:3,2-b]diindoles, and dihydrodiazepino[1,2-a:4,3-a]diindoles, resulting from intramolecular ring opening-expansion cyclisation processes of their parent oxiranes and aziridines. Regiochemical and stereochemical aspects of the reactions are reported together with...[Show more]

CollectionsANU Research Publications
Date published: 2018
Type: Journal article
Source: Organic and Biomolecular Chemistry
DOI: 10.1039/c8ob00865e


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