Synthesis 2003(13): 2096-2100  
DOI: 10.1055/s-2003-41452
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Facile Route to Symmetrical and Unsymmetrical Cycloalkeno[c]fused 2,2′-Bipyridine Ligands via Inverse Electron Demand Diels-Alder Reaction of 5,5′-bi-1,2,4-Triazines [1]

Danuta Branowska*
Department of Chemistry, University of Podlasie, 3-go Maja 54, 08 -110 Siedlce, Poland
Fax: +48(25)6431106; e-Mail: [email protected];
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Publikationsverlauf

Received 7 March 2003
Publikationsdatum:
10. September 2003 (online)

Abstract

A series of 6,6′-bisfunctionalized symmetrical cycloal­keno[c]fused 2,2′-bipyridines 4a-h or unsymmetrical cycloal­keno[c]fused 2,2′-bipyridines 6a-g is described. They were prepared by the Diels-Alder reaction of 3,3′-disubstituted 5,5′-bi-1,2,4-triazines 2a,b with cyclic enamines 3a-d. The regioselective reaction of 1-vinylimidazole (3e) with 2a leads to 5-(2-pyridyl)-1,2,4-triazine 9 which undergoes Diels-Alder reaction with cyclic enamines 3a-d to give unsymmetrical 2,2′-bipyridines 10a-d with one cycloalkene ring attached.

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