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Synthesis 2003(4): 0577-0583
DOI: 10.1055/s-2003-37658
PAPER
© Georg Thieme Verlag Stuttgart · New York

Enamine-Functionalized Oligopyridines as Convenient Intermediates for the Synthesis of Carbaldehyde Derivatives

Lydie Viaua, Katell Sénéchala, Olivier Maurya, Jean-Paul Guégana, Philippe Dupaua, Loïc Toupetb, Hubert Le Bozec*a
a Organométalliques et Catalyse : Chimie et Electrochimie Moléculaires, UMR 6509 CNRS-Université de Rennes 1, Institut de Chimie de Rennes, Campus de Beaulieu, 35042 Rennes Cedex, France
Fax: +33(2)99286939; e-Mail: lebozec@univ-rennes1.fr;
b Groupe de la Matière Condensée et Matériau, UMR 6626 CNRS-Université de Rennes 1, Campus de Beaulieu, 35042 Rennes Cedex, France
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Publication History

Received 27 September 2002
Publication Date:
07 March 2003 (online)

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Abstract

A series of enamine-substituted bipyridine, biquinoline and o-phenanthroline chromophores has been synthesized and fully characterized. The para regioselectivity of the functionalization is discussed on the basis of 2D NOESY correlation and X-ray diffraction analysis. Absorption and emission spectroscopic studies allow a comparison of the acceptor strength of the heterocyclic core (biquinoline > phenanthroline > bipyridine). These enamine derivatives are key intermediates for a straightforward preparation of the corresponding dicarbaldehyde-bisimine compounds.

Key words

heterocycles - imines - ligands - aldehydes - chromophores

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Other sources of NaIO4 gave only poor yield.