Issue 15, 2010

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

Abstract

The CAN-catalyzed three-component between reaction between primary amines, β-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 γ-alkylation/ring-closing metathesis sequence.

Graphical abstract: 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

Supplementary files

Article information

Article type
Paper
Submitted
29 Mar 2010
Accepted
19 May 2010
First published
09 Jun 2010

Org. Biomol. Chem., 2010,8, 3426-3436

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

P. A. Suryavanshi, V. Sridharan and J. C. Menéndez, Org. Biomol. Chem., 2010, 8, 3426 DOI: 10.1039/C004703A

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