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Note | Special issue | Vol 67, No. 2, 2006, pp.815-822
Published online, 14th October, 2005
DOI: 10.3987/COM-05-S(T)79
Cycloaddition Reactions of 1-Azadienes Derived from Hydrazones with Electron-deficient Dienophiles

Francisco Palacios,* Domitila Aparicio, Yago Lópes, and Jesús M. de los Santos

*Departamento de Química Orgánica I, Facultad de Farmacia, Universidad del País Vasco, Apto. 450, 01080 Vitoria, Spain


The aza-Diels-Alder reaction of 1-aza-1,3-butadienes derived from hydrazones, with electron-deficient dienophiles is reported. When there is not substitution at C-2 in the starting 1-azadiene, fused-pyridine derivatives are obtained. However, the use of 1-azadienes substituted with a methyl group at C-2 gave the corresponding pyridazinone derivative.