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

Lydie Viau; Katell Sénéchal; Olivier Maury; Jean-Paul Guégan; Philippe Dupau; Loïc Toupet; Hubert Le Bozec

doi:10.1055/s-2003-37658

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

Lydie Viau^a, Katell Sénéchal^a, Olivier Maury^a, Jean-Paul Guégan^a, Philippe Dupau^a, Loïc Toupet^b, 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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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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