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A novel one-pot synthesis of annulated 2,2′-bipyridine ligands by inverse electron demand Diels–Alder reaction of 5,5′-bi-1,2,4-triazines

✍ Scribed by Andrzej Rykowski; Danuta Branowska; Joanna Kielak

Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 102 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)00436-6

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✦ Synopsis

The Diels-Alder reaction of 5,5 -bi-1,2,4-triazines with cyclic enamines in the absence of a solvent leads to a range of symmetrical, annulated 2,2 -bipyridines in good yield. When the reaction is carried out in boiling dioxane only 5-(heteroaryl)1,2,4-triazines are formed. The latter, bearing methylsulfanyl substituents, are oxidized with potassium permanganate to the corresponding methylsulfonyl derivatives, which easily undergo Diels-Alder reactions with different enamines to give unsymmetrical, annulated 2,2 -bipyridines.

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