Organic & Biomolecular Chemistry 2010-08-07

Expedient, one-pot preparation of fused indoles via CAN-catalyzed three-component domino sequences and their transformation into polyheterocyclic compounds containing pyrrolo[1,2-a]azepine fragments.

Padmakar A Suryavanshi, Vellaisamy Sridharan, J Carlos Menéndez

Index: Org. Biomol. Chem. 8(15) , 3426-36, (2010)

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Abstract

The CAN-catalyzed three-component between reaction between primary amines, beta-dicarbonyl compounds and naphthoquinones or 2-bromonaphthoquinones afforded, respectively, 5-hydroxybenzo[g]indoles and benzo[f]indole-4,9-diones, the former of which were transformed into tetracyclic azepino[1,2-a]benzo[g]indole systems through a gamma-alkylation/ring-closing metathesis sequence.