Tetrahedron Letters

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

A Rykowski, D Branowska, J Kielak

Index: Rykowski, Andrzej; Branowska, Danuta; Kielak, Joanna Tetrahedron Letters, 2000 , vol. 41, # 19 p. 3657 - 3659

Full Text: HTML

Citation Number: 55

Abstract

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 ...