Preparation and reactions of 3-phosphinyl-1-aza-1,3-butadienes. Synthesis of phosphorylated pyridine and pyrazole derivatives |
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| Authors: | Francisco Palacios,Domitila Aparicio,Jesú s M. de los Santos |
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| Affiliation: | a Departamento de Química Orgánica I, Facultad de Farmacia, Universidad del País Vasco, Apartado 450, 01080 Vitoria, Spain
b Departamento de Física Aplicada II, Facultad de Farmacia, Universidad del País Vasco, Apartado 450, 01080 Vitoria, Spain |
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| Abstract: | 3-Phosphinyl 1-aza-1,3-butadienes 2 are obtained by aldol condensation between hydrazonoalkyl phosphine oxides and N,N-dimethylformamide dimethyl acetal. Transamination reaction of these azadienes with amines yields functionalized 1-aza-1,3-butadienes 3. Cycloaddition processes of these azadienes 2a with electron-poor dienophiles to give phosphorylated pyridine derivatives 9 and 15 are also reported, while intramolecular cyclization reaction of heterodiene 2b affords phosphorylated pyrazole 17. |
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| Keywords: | Hydrazones 1-Aza-1, 3-buladienes Phosphorylated heterocycles Aza-Diels-Alder |
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