Issue 3, 2004
From the journal:

Organic & Biomolecular Chemistry

Metallation of pyridines and quinolines in the presence of a remote carboxylate group. New syntheses of heterocyclic quinones

Anne-Sophie Rebstock,a   Florence Mongin,*a   François Trécourta  and  Guy Quéguinera  

* Corresponding authors

a Laboratoire de Chimie Organique Fine et Hétérocyclique, IRCOF, UMR 6014, Place E. Blondel, BP 08, 76131 Mont-Saint-Aignan, France
E-mail: florence.mongin@insa-rouen.fr

Abstract

2-(3- and 2-Pyridylcarbonyl)benzoic acids (2, 3), 2-(2-pyridylcarbonyl)thiophene-3-carboxylic acid (6), 2-(3-quinolylcarbonyl)benzoic acid (10), and most of the corresponding esters (compounds 1, 7 and 9) are readily synthesized and involved in a deprotonation–condensation sequence. Biologically active aza-anthraquinones such as benzo[g]isoquinoline-5,10-dione (2-azaanthraquinone, 4) and benzo[g]quinoline-5,10-dione (1-azaanthraquinone, 5) are prepared using the strategy. Extension to other heterocyclic quinones such as thieno[3,2-g]quinoline-4,9-dione (8) and benzo[j]phenanthridine-7,12-dione (11) is also investigated.

Graphical abstract: Metallation of pyridines and quinolines in the presence of a remote carboxylate group. New syntheses of heterocyclic quinones

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Article information

DOI
https://doi.org/10.1039/B312723K
Article type
Paper
Submitted
14 Oct 2003
Accepted
14 Nov 2003
First published
11 Dec 2003

Org. Biomol. Chem., 2004,2, 291-295

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Metallation of pyridines and quinolines in the presence of a remote carboxylate group. New syntheses of heterocyclic quinones

A. Rebstock, F. Mongin, F. Trécourt and G. Quéguiner, Org. Biomol. Chem., 2004, 2, 291 DOI: 10.1039/B312723K

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