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  4. <i>Amino-Claisen</i> Rearrangements and <i>Diels-Alder</i> Reactions of Ketene N,O-Acetals: Reactivity Studies. On the Way to a Novel Tandem Process?
 
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<i>Amino-Claisen</i> Rearrangements and <i>Diels-Alder</i> Reactions of Ketene N,O-Acetals: Reactivity Studies. On the Way to a Novel Tandem Process?

Auteur(s)
Neuschütz, Klaus
Simone, Jean-Mary
Thyrann, Thomas
Neier, Reinhard 
Institut de chimie 
Date de parution
2000
In
Helvetica Chimica Acta, Wiley, 2000/83/10/2712 - 2737
Résumé
We report the synthesis of <i>N</i>-benzyl-<i>N</i>-[(<i>E</i>)-buta-1,3-dienyl]propanamide (<b>6</b>) and its corresponding O-silyl-substituted ketene N,O-acetal <b>7</b> and their <i>Diels-Alder</i> reaction. Propanamide <b>6</b> reacted smoothly, whereas the yield obtained from <b>7</b> was low, probably due to polymerization of the dienophile induced by electron transfer. The ketene N,O-acetals <b>27a - g</b> were synthesized starting from the corresponding benzamides <b>25a - e</b> (<i>Scheme 9</i>). The ketene N,O-acetals <b>27a - g</b> showed increased stabilities and underwent amino-<i>Claisen</i> rearrangements under thermal conditions. Using catalysts, interesting side reactions leading either to the annulated systems <i>rac</i>-<b>35 - 37</b> or to a β-lactam <i>rac</i>-<b>34</b> were observed.
Identifiants
https://libra.unine.ch/handle/123456789/17750
Type de publication
journal article
Dossier(s) à télécharger
 main article: Neusch_tz_Klaus_-_Amino-Claisen_Rearrangements_and_Diels-Alder_Reactions_20070706.pdf (655.03 KB)
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