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

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...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2010-08, Vol.8 (15), p.3426-3436
Main Authors: Suryavanshi, Padmakar A, Sridharan, Vellaisamy, Menéndez, J Carlos
Format: Article
Language:English
Subjects:
Alkylation
Azepines - chemistry
Catalysis
Cerium - chemistry
Hydrogen-Ion Concentration
Indoles - chemical synthesis
Indoles - chemistry
Kinetics
Nitrates - chemistry
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Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c004703a