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Synthesis of Tetrahydropyridines by an Aza-Diels-Alder Reaction
J. Vicario, D. Aparicio, F. Palacios*
Universidad del País Vasco, Apartado, Spain
19 August 2011 (online)
Nitrogen-containing heterocycles are widespread in natural products and pharmaceuticals. The Diels-Alder reaction utilizing imines (aza-Diels-Alder) is perhaps the most direct method for accessing six-membered heterocycles (see Review below). In the present communication, the authors report on the use of 1-azadienes as dienes in the inverse-electron-demand aza-Diels-Alder reaction with enamine dienophiles.
Review: P. Buonora, J. C. Olsen, T. Oh Tetrahedron 2001, 57, 6099-6138.