Cycloaddition Reactions of Phosphorylated 1,2-Diaza-1,3-butadienes with Olefins: Regioselective Synthesis of Pyridazine Derivatives

Cycloaddition Reactions of Phosphorylated 1,2-Diaza-1,3-butadienes with Olefins: Regioselective Synthesis of Pyridazine Derivatives

The aza‐Diels–Alder reaction of 4‐phosphinyl‐ and 4‐phosphonyl‐1,2‐diaza‐1,3‐butadienes with styrene, cyclopentadiene, dihydrofuran and norbornadiene is reported. Monocyclic, bicyclic and polycyclic tetrahydropyridazines containing a phosphane oxide or a phosphonate substituent are obtained. The for...

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Veröffentlicht in:European Journal of Organic Chemistry 2005-03, Vol.2005 (6), p.1142-1147
Hauptverfasser: Palacios, Francisco, Aparicio, Domitila, López, Yago, de los Santos, Jesús M., Alonso, Concepción
Format: Artikel
Sprache:eng
Schlagworte:
Cycloadditions
Diazabutadienes
Fused-ring systems
Hydrazones
Nitrogen heterocycles
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Zusammenfassung:The aza‐Diels–Alder reaction of 4‐phosphinyl‐ and 4‐phosphonyl‐1,2‐diaza‐1,3‐butadienes with styrene, cyclopentadiene, dihydrofuran and norbornadiene is reported. Monocyclic, bicyclic and polycyclic tetrahydropyridazines containing a phosphane oxide or a phosphonate substituent are obtained. The formation of cycloadducts can be explained by an endo transition state in the cycloaddition process of these heterodienes with styrene, cyclopentadiene, dihydrofuran, and by means of an exo transition state in the case of norbornadiene. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200400675