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Issue 8, 2008
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Solvent-dependent oxidations of 5- and 6-azaindoles to trioxopyrrolopyridines and functionalised azaindoles

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Abstract

A regioselective synthesis of 4,7-dimethoxy 5- and 6-azaindoles 2 has been achieved, based on the appropriate choice of ortho-directing or ortho-repulsing groups in the formylation of a pyridine ring. Studies on the regioselectivity of the formylation step and on the preparation of azidoacrylate intermediates 4 are described in this paper. The reactivity of the 5- and 6-azaindole structures towards BBr3-mediated selective monodemethylation and oxidative demethylation reactions were also investigated. The regioselectivity of the deprotection was confirmed using a chemical approach. Oxidation reactions were then carried out on either dimethoxy- or hydroxymethoxyazaindoles, in different solvents, using [bis(trifluoroacetoxy)iodo]benzene. In acetonitrilewater, trioxopyrrolopyridines 12 were obtained, whereas the formation of functionalised azaindoles 17 was observed in acetonitrilemethanol. The tautomeric structure of the trioxopyrrolopyridines was proved by X-ray diffraction analysis.

Graphical abstract: Solvent-dependent oxidations of 5- and 6-azaindoles to trioxopyrrolopyridines and functionalised azaindoles

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Supplementary files

Article information


Submitted
02 Jan 2008
Accepted
07 Feb 2008
First published
28 Feb 2008

Org. Biomol. Chem., 2008,6, 1364-1376
Article type
Paper

Solvent-dependent oxidations of 5- and 6-azaindoles to trioxopyrrolopyridines and functionalised azaindoles

Z. Mahiout, T. Lomberget, S. Goncalves and R. Barret, Org. Biomol. Chem., 2008, 6, 1364
DOI: 10.1039/B719776D

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